IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
|
출원번호 |
US-0117670
(2002-04-04)
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발명자
/ 주소 |
- Shah, Pankaj
- Gros, Hå
- kan
- Lindholm, Bengt
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출원인 / 주소 |
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대리인 / 주소 |
Scully, Scott, Murphy & Presser
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인용정보 |
피인용 횟수 :
26 인용 특허 :
4 |
초록
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The present invention is directed to a process and product by process for preparing a carbohydrate polymer which comprises polymerizing a sugar at a temperature below the point of substantial decomposition thereof and under reduced pressure in the presence of a catalytic effective amount of an organ
The present invention is directed to a process and product by process for preparing a carbohydrate polymer which comprises polymerizing a sugar at a temperature below the point of substantial decomposition thereof and under reduced pressure in the presence of a catalytic effective amount of an organic acid selected from the group consisting of a monocarboxylic acid, a lactone of a monocarboxylic acid and arylol, while removing water formed during said polymerization, said organic acid being non-volatile and having only one acidic functionality and having no amino groups thereon.
대표청구항
▼
1. A process for preparing a carbohydrate polymer which comprises polymerizing a sugar selected from the group consisting of a monosaccharide, dissacharide, oligosaccharide and hydrolysate of a carbohydrate polymer at a temperature below the point of substantial decomposition of said sugar and under
1. A process for preparing a carbohydrate polymer which comprises polymerizing a sugar selected from the group consisting of a monosaccharide, dissacharide, oligosaccharide and hydrolysate of a carbohydrate polymer at a temperature below the point of substantial decomposition of said sugar and under reduced pressure and under conditions effective for polymerization in the presence of a catalytic effective amount of an organic acid thereof while removing water formed during said polymerization, said organic acid being a monocarboxylic acid or lactone thereof or arylol. 2. The process according to claim 1 wherein said organic acid is present in a range from 0.01 to about 25 mol % relative to the sugar. 3. The process according to claim 2 wherein said organic acid is present in amounts ranging from about 0.01 to about 1 mol %. 4. The process according to claim 1 wherein the organic acid is an arylol. 5. The process according to claim 4 wherein the organic acid is a phenol, alkyl substituted phenol or alkenyl substituted phenol, wherein the alkyl and alkenyl groups each independently contain 1-6 carbon atoms. 6. The process according to claim 1 wherein the organic acid is a monocarboxylic acid. 7. The process according to claim 1 wherein the organic acid is a steroid monocarboxylic acid, sugar monocarboxylic acid, aryl monocarboxylic acid, aralkyl monocarboxylic acid, aliphatic monocarboxylic acid, cycloaliphatic monocarboxylic acid, or heterocyclic monocarboxylic acid or heterocyclic alkyl monocarboxylic acid or combination thereof or a lactone of the organic acid. 8. The process according to claim 1 wherein the organic acid is aldouronic acid or aldonic acid. 9. The process according to claim 7 wherein the steroid monocarboxylic acid has the formula:wherein each R 3 , R 4 , R 5 and R 6 are independently hydrogen, hydroxy, lower alkoxy, lower alkyl, oxo, carboxy or lower alkyl substituted with carboxy,n is 0-4;p is 0-4; andn and q are independently 0-2, with the proviso that only one of R 3 , R 4 , R 5 or R 6 contains a carboxy group. 10. The process according to claim 9 wherein R 6 is an alkyl group substituted by carboxy, and p is 1. 11. The process according to claim 7 wherein the steroid monocarboxylic acid has the formula 12. The process according to claim 1 wherein the organic acid is a monocarboxylic fatty acid. 13. The process according to claim 1 wherein the organic acid has the formula RCOOH wherein R is alkyl containing 1-24 carbon atoms or alkenyl containing 2-24 carbon atoms and 1, 2, 3 or 4 carbon-carbon double bonds, cycloaliphatic containing 3-18 ring carbon atoms, aryl containing 6-18 ring carbon atoms, arylalkyl containing 6-18 ring carbon atoms and 1-6 carbon atoms bridging the aryl group and the COOH, heterocyclic, heterocyclic alkyl, heteroaromatic or heteroaromatic alkyl, wherein heterocyclic contains 3-18 ring atoms and at least 1 ring and at most 4 ring heteroatoms, and the remainder are carbon ring atoms, heteroaromatic contains 5-18 ring atoms and at least 1 and at most 4 ring heteroatoms, and the remainder are carbon ring atoms wherein the heteroatom O or S; heterocylic alkyl is an alkyl group containing 1-6 carbon atoms bridging a heterocyclic group and the COOH, and heteroaromatic alkyl is an alkyl group containing 1-6 carbon atoms bridging the heteroaromatic group and the COOH group. 14. The process according to claim 1 wherein the organic acid is benzoic acid, salicylic acid or acetyl salicylic acid. 15. The process according to claim 1 wherein the organic acid is a lactone of a monocarboxylic acid. 16. The process according to claim 15 wherein the lactone is glucono delta lactone. 17. The process according to claim 1 wherein from about 5 to 20% by weight of a food acceptable polyol is added prior to or during said polymerization. 18. The process according to claim 17 wherein the polyol is selected from the group consisting of sorbitol, glycerol, erythritol, xylitol, mannitol and galactito l. 19. The process according to claim 18 wherein the polyol is sorbitol. 20. The process according to claim 1 wherein polymerization occurs at a pressure of less than about 300 mm Hg. 21. The process according to claim 1 wherein the product is polydextrose. 22. The process according to claim 1 wherein the organic acid is glycolic acid, pyruvic acid or lactic acid. 23. The process according to claim 1 wherein the organic acid is a monocarboxylic acid or lactone thereof. 24. The process according to claim 19 wherein the product is polydextrose. 25. The process according to claim 1 wherein the product is polydextrose or polymaltose and the process comprises polycondensing a sugar selected from the group consisting of D-glucose and maltose at a temperature ranging from about 140° C. to about 295° C. and at reduced pressure in the presence of a catalytic effective amount of a said organic acid, while removing water formed during said polymerization organic acid being. 26. The process according to claim 25 wherein the process comprises melting the sugar at a temperature ranging from about 140° C. to about 295° C. and at reduced pressure in the presence of a catalytic effective amount of an organic acid, while removing water formed during said polymerization. 27. The process according to claim 25 wherein said organic acid is present in about 0.01 to about 25 mol % relevant to the sugar. 28. The process according to claim 27 wherein said organic acid is present in amounts ranging from about 0.01 mol % to about 1 mol %. 29. The process according to claim 25 wherein the organic acid is a steroid monocarboxylic acid, sugar monocarboxylic acid, aryl monocarboxylic acid, aralkyl monocarboxylic acid, aliphatic monocarboxylic acid, cycloaliphatic monocarboxylic acid, or heterocyclic monocarboxylic acid or heterocyclic alkyl monocarboxylic acid. 30. The process according to claim 25 wherein the organic acid is an arylol. 31. The process according to claim 30 wherein the organic acid is a phenol, alkyl substituted phenol or alkenyl substituted phenol, wherein the alkyl and alkenyl groups contain 1-6 carbon atoms. 32. The process according to claim 25 wherein the organic acid is a monocarboxylic acid or a lactone thereof. 33. The process according to claim 32 wherein the organic acid is a monocarboxylic acid. 34. The process according to claim 32 wherein the organic acid is a lactone of a monocarboxylic acid. 35. The process according to claim 25 wherein the organic acid is a sugar monocarboxylic acid. 36. The process according to claim 35 wherein the monocarboxylic acid is aldouronic acid or aldonic acid. 37. The process according to claim 29 wherein the steroid monocarboxylic acid has the formula:wherein each R 3 , R 4 , R 5 and R 6 are independently hydrogen hydroxy, lower alkoxy, lower alkyl, oxo, carboxy or lower alkyl substituted with carboxy,n is 0-4;p is 0-4; andn and q are independently 0-2, with the proviso that only one of R 3 , R 4 , R 5 or R 6 contains a carboxy group. 38. The process according to claim 25 wherein the monocarboxylic acid is a fatty monocarboxylic acid. 39. The process according to claim 25 wherein the monocarboxylic acid has the formula RCOOH wherein R is alkyl containing 1-24 carbon atoms or alkenyl containing 2-24 carbon atoms and 1, 2, 3 or 4 carbon-carbon double bonds, cycloaliphatic containing 3-18 ring carbon atoms, aryl containing 6-18 ring carbon atoms, arylalkyl containing 6-18 ring carbon atoms and 1-6 carbon atoms bridging the aryl group and the COOH, heterocyclic, heterocyclic alkyl, heteroaromatic or heteroaromatic alkyl, wherein heterocyclic contains 3-18 ring atoms and at least 1 ring and at most 4 ring heteroatoms, and the remainder are carbon ring atoms; heteroaromatic contains 5-18 ring atoms and at least 1 and at most 4 ring heteroatoms, and the remainder are carbon ring atoms wherein the heteroatom is O, S or N; heterocylic alkyl is an alkyl group containing 1-6 carbo n atoms bridging a heterocyclic group and the COOH; and heteroaromatic alkyl is an alkyl group containing 1-6 carbon atoms bridging the heteroaromatic group and the COOH group. 40. The process according to claim 25 wherein the organic acid is benzoic acid, salicylic acid or acetyl salicylic acid. 41. The process according to claim 25 wherein a polyol is additionally present. 42. The process according to claim 25 wherein the organic acid is a lactone of a sugar monocarboxylic acid. 43. The process according to claim 42 wherein the lactone is glucono delta lactone. 44. The process according to claim 25 wherein from about 5 to 20% by weight of a food acceptable polyol is added prior to or during said polymerization. 45. The process according to claim 44 wherein the polyol is selected from the group consisting of sorbitol, glycerol, erythritol, xylitol, mannitol and galactitol. 46. The process according to claim 45 wherein the polyol is sorbitol. 47. The process according to claim 25 wherein the polymerization occurs at a pressure of less than about 300 mm Hg. 48. The process according to claim 25 wherein the organic acid is an α-keto monocarboxylic acid or an α-hydroxy monocarboxylic acid. 49. The process according to claim 48 wherein the monocarboxylic acid is glycolic acid, pyruvic acid or lactic acid. 50. The process according to claim 1 wherein the carbohydrate polymer is subjected to purification. 51. The process according to claim 50 wherein purification comprises neutralizing the acid associated therewith. 52. The process according to claim 51 wherein neutralizing comprises contacting the carbohydrate polymer with base. 53. The process according to claim 51 wherein neutralizing comprises dialyzing the carbohydrate polymer. 54. The process according to claim 51 wherein neutralizing comprises making a concentrated solution of the carbohydrate polymer and passing said concentrated solution through an adsorbent resin. 55. The process according to claim 54 wherein the adsorbent resin is an ion exchange resin. 56. The process according to claim 50 wherein the carbohydrate polymer is contacted with molecular sieves. 57. The process according to claim 1 wherein the carbohydrate polymer is hydrogenated. 58. The process according to claim 57 wherein the carbohydrate polymer is subjected to purification and hydrogenation. 59. The process according to claim 58 wherein purification comprises neutralizing the acid associated with the carbohydrate polymer. 60. The process according to claim 59 wherein neutralizing comprises passing the carbohydrate polymer or the hydrogenated carbohydrate polymer through an ion-exchange resin. 61. The process according to claim 25 wherein the product is subjected to purification. 62. The process according to claim 61 wherein the purification comprises neutralizing the acid associated with the product. 63. The process according to claim 62 wherein neutralizing comprises contacting the product with base. 64. The process according to claim 62 wherein neutralizing comprises dialyzing the product. 65. The process according to claim 62 wherein neutralization comprises making a concentrated solution of the product and passing said concentrated solution through an adsorbent resin. 66. The process according to claim 65 wherein the adsorbent resin is an ion exchange resin. 67. The process according to claim 61 wherein the product is contacted with molecular sieves. 68. The process according to claim 25 wherein the product is hydrogenated. 69. The process according to claim 68 wherein the product is subjected to purification and hydrogenation. 70. The process according to claim 69 wherein purification comprises neutralizing the acid associated with the product or hydrogenated product. 71. The process according to claim 70 wherein neutralizing comprises making a concentrated solution of the product or hydrogenated product and passing the concentrated solution through an ion-exchange resin. 72. The produc t of claim 1. 73. The product of claim 25. 74. The product of claim 50. 75. A carbohydrate polymer associated with a monocarboxylic acid or lactone thereof. 76. The carbohydrate polymer of claim 75 which is further associated with a polyol. 77. The carbohydrate polymer according to claim 76 wherein the polyol is sorbitol. 78. A substantially purified product of any one of claims 75 - 77 . 79. The carbohydrate polymer according to claim 75 or 76 which is purified by contacting the same with a base in sufficient quantity to substantially neutralize the acid associated therewith. 80. The carbohydrate polymer according to claim 75 or 76 which is passed through an adsorbent resin. 81. The carbohydrate polymer according to claim 80 wherein the adsorbent resin is an ion exchange resin. 82. The carbohydrate polymer according to claim 75 or 76 which is contacted with molecular sieve. 83. The carbohydrate polymer according to claim 82 which is subjected to purification. 84. The carbohydrate polymer according to claim 83 wherein the purification comprises neutralizing the acid associated therewith. 85. The carbohydrate polymer according to claim 84 wherein neutralizing comprises making a concentrated solution of the carbohydrate polymer and passing the concentrated solution through an ion exchange resin. 86. The carbohydrate polymer according to any one of claims 75 - 77 which is hydrogenated. 87. The carbohydrate polymer according to any one of claims 75 - 77 wherein the carbohydrate polymer is polydextrose or hydrogenated polydextrose. 88. A process for administering an edible organic acid to an animal which comprises(a) polymerizing a sugar selected from the group consisting of a monosaccharide, disaccharide, oligosaccharide and hydrolysate of a carbohydrate polymer at a temperature below the point of substantial decomposition of said sugar and under reduced pressure under polymerization effective conditions in the presence of a catalytic effective amount of an edible organic acid thereof while removing water formed during said polymerization, said organic acid being non-volatile, wherein said organic acid is a monocarboxylic acid or lactone thereof or arylol;(b) adding the product of (a) to foodstuff or feed; and(c) administering the foodstuff or feed of (b) to said animal. 89. The process according to claim 88 wherein the animal is a human. 90. A process of making a food which comprises(a) polymerizing a sugar selected from the group consisting of a monosaccharide, disaccharide, oligosaccharide and hydrolysate of a carbohydrate polymer at a temperature below the point of substantial decomposition of said sugar and under reduced pressure and under polymerization effective conditions in the presence of a catalytic effective amount of an edible organic acid thereof while removing water formed during said polymerization, said organic acid being non-volatile, wherein said organic acid is a monocarboxylic acid or lactone thereof or arylol:(b) adding the product of (a) to foodstuff or feed. 91. A foodstuff or feed containing a polymerized carbohydrate polymer prepared by the process comprising:(a) polymerizing a sugar selected from the group consisting of a monosaccharide, disaccharide, oligosaccharide and hydrolysate of a carbohydrate polymer at a temperature below the point of substantial decomposition of said sugar and under reduced pressure under polymerization effective conditions in the presence of a catalytic effective amount of an edible organic acid thereof while removing water formed during said polymerization, said organic acid being non-volatile, said organic acid being a monocarboxylic acid or lactone thereof or arylol; and(b) adding the product of (a) to foodstuff or feed. 92. The process according to claim 1 wherein the monocarboxylic acid is a keto acid or hydroxy acid of the formula:whereinR 7 and R 8 are independently lower alkyl, aryl or lower arylalkyl and n 1 is 0 or 1. 93. The process according to claim 92 wherei n n 1 is 0. 94. The process according to claim 25 wherein the monocarboxylic acid is a keto acid or hydroxy acid of the formula:whereinR 7 and R 8 are independently lower alkyl, aryl or lower arylalkyl and n 1 is 0 or 1. 95. The process according to claim 94 wherein n 1 is 0.
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