CA1085107A - Starch paste - Google Patents
Starch pasteInfo
- Publication number
- CA1085107A CA1085107A CA255,115A CA255115A CA1085107A CA 1085107 A CA1085107 A CA 1085107A CA 255115 A CA255115 A CA 255115A CA 1085107 A CA1085107 A CA 1085107A
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- starch
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- weight
- starch paste
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
- C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Glanulating (AREA)
- Fats And Perfumes (AREA)
- Biological Depolymerization Polymers (AREA)
- Formation And Processing Of Food Products (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
IMPROVED STARCH PASTE
Abstract of the Disclosure The invention concerns an improved starch paste having excellent disintegration properties, which is useful as a binder for the preparation of granules in the fields of foodstuffs, medicines and the like.
The improved starch paste is prepared by treating a natural starch or an .alpha.-starch with an organic solvent selected from alcohols having 1 to 3 carbon atoms, acetone and mixtures thereof, before or after converting the starch into the starch paste.
Abstract of the Disclosure The invention concerns an improved starch paste having excellent disintegration properties, which is useful as a binder for the preparation of granules in the fields of foodstuffs, medicines and the like.
The improved starch paste is prepared by treating a natural starch or an .alpha.-starch with an organic solvent selected from alcohols having 1 to 3 carbon atoms, acetone and mixtures thereof, before or after converting the starch into the starch paste.
Description
/
~L~BS~
The present invention relates to improved starch products, such as starch paste, havlng good dis-tintergration properties, and to a process for prepar:Lng such products.
Starch paste has been wide]y used as a binder for use with foodstuffs and medicines. ~lowever, when starch paste is used as a binder in a wet granulating process, for example, it has the disadvantage that the granules obtained have inferior disintegration proper-ties. When the granules contain a medicament, the granules should preferably be disintegrated in the gastro-intestinal tract promptly after administration and so that the medicament contained therein can be quickly . . .
dissolved into gastric or intestinal Juices. From this standpoint, conventional starch paste is not necessarily preferable as the binder for medicinal granules. On the other hand, starch pastestill has some advantages in that it is inexpensive and harmless to the human body and it shows few interactions with most medicaments.
Also, there is usually no difficulty, such as the for-mation of an emulsion, in analytical procedures, such as the extraction thereof, because the starch paste is practically chemically inactive. Accordingly, if the disintegration properties of the conventional starch paste could be improved, it would be more widely used as a binder in various fields.
Conventional starch paste is usually prepared ` by one of the following processes: (1) a natural starch, which has not been converted into an ~-starch, is dis-` 30 persed into water and the dispersion is heated so as to ~`~ convert the natural starch into an ~-starch, (2) a natural : ' ~ '~
35~7 starch, which has not been converted into an ~-starch, is dispersed in a small amount of water and hot water at 80C
or higher is added thereto, and t3) lried (~-starch is dispersed in water.
The present inventors have attempted to improve the disintegration properties of conventional starch paste.
Firstly, they tried to improve the disintegration properties by radically changing the gelatinization temperature, the concentration of the starch paste, the temperature of the starch paste or the like in the - conventional processes, but no satisactory result could be obtained. It has now unexpectedly been found that the disintegration properties of starch paste can be significantly improved by adding an alcohol having 1 to 3 carbon atoms and/or acetone to a dispersion of starch in water, and that granules having good disintegration properties can be obtained by using this improved starch ~ paste as a binder.
; According to one aspect of the invention there is provided a process for preparing granules having im-~ proved disintegration properties, which comprises mixing ; materials to be granulated with a starch paste comprising 5 to 20 % by weight of a gelatinized starch and 95 to 80 %
by weight of a mixture of water and an organic solvent selected from the group consisting of acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereof wherein said organic solvent is present in a ratio of 20 to 50 ~ by weight based on the whole weight of the mixture of the water and the organic solvent, and then granulating 3~ the resulting mixture by a wet granulating process.
According to another aspect of the invention there is
~L~BS~
The present invention relates to improved starch products, such as starch paste, havlng good dis-tintergration properties, and to a process for prepar:Lng such products.
Starch paste has been wide]y used as a binder for use with foodstuffs and medicines. ~lowever, when starch paste is used as a binder in a wet granulating process, for example, it has the disadvantage that the granules obtained have inferior disintegration proper-ties. When the granules contain a medicament, the granules should preferably be disintegrated in the gastro-intestinal tract promptly after administration and so that the medicament contained therein can be quickly . . .
dissolved into gastric or intestinal Juices. From this standpoint, conventional starch paste is not necessarily preferable as the binder for medicinal granules. On the other hand, starch pastestill has some advantages in that it is inexpensive and harmless to the human body and it shows few interactions with most medicaments.
Also, there is usually no difficulty, such as the for-mation of an emulsion, in analytical procedures, such as the extraction thereof, because the starch paste is practically chemically inactive. Accordingly, if the disintegration properties of the conventional starch paste could be improved, it would be more widely used as a binder in various fields.
Conventional starch paste is usually prepared ` by one of the following processes: (1) a natural starch, which has not been converted into an ~-starch, is dis-` 30 persed into water and the dispersion is heated so as to ~`~ convert the natural starch into an ~-starch, (2) a natural : ' ~ '~
35~7 starch, which has not been converted into an ~-starch, is dispersed in a small amount of water and hot water at 80C
or higher is added thereto, and t3) lried (~-starch is dispersed in water.
The present inventors have attempted to improve the disintegration properties of conventional starch paste.
Firstly, they tried to improve the disintegration properties by radically changing the gelatinization temperature, the concentration of the starch paste, the temperature of the starch paste or the like in the - conventional processes, but no satisactory result could be obtained. It has now unexpectedly been found that the disintegration properties of starch paste can be significantly improved by adding an alcohol having 1 to 3 carbon atoms and/or acetone to a dispersion of starch in water, and that granules having good disintegration properties can be obtained by using this improved starch ~ paste as a binder.
; According to one aspect of the invention there is provided a process for preparing granules having im-~ proved disintegration properties, which comprises mixing ; materials to be granulated with a starch paste comprising 5 to 20 % by weight of a gelatinized starch and 95 to 80 %
by weight of a mixture of water and an organic solvent selected from the group consisting of acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereof wherein said organic solvent is present in a ratio of 20 to 50 ~ by weight based on the whole weight of the mixture of the water and the organic solvent, and then granulating 3~ the resulting mixture by a wet granulating process.
According to another aspect of the invention there is
2 -.
101351~7 is provided in a wet granulating process for preparing granules having improved disintegration properties, the improvement which comprises using a starch paste binder prepared by admixing an organic solvent selected from the group consisting o~ acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereoE with a starch paste.
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The invention inclu(les lmproved starcll pastes produced by tl~e process or method deEined a'bove, An advantage of the present lnvention, at least in the preferred forms, ls that it can provide an improved starch paste having good dislntegration proper-ties, which is therefore useful as a binder for gran~les.
~ nother advantage of the invention, at least in the preferred forms, that it can provide a method for improving the disintegration properties of conventional starch pastes.
A sti'll futher advantage of the invention is that it can provide improved granules for foodstuffs, medicines or the like.
These and other advantages of the inventLon will become apparent from the following description of the preferred embodiments of the invention.
The improved starch paste of the present invention comprises 5 to 20% by weight of a gelatinized starch and 95 to 80% by weight of a mixture of water and an organic solvent selected from alcohols having 1 to 3 ' carbon atoms, acetone and mi~tures thereof, wherein the organic solvent is contained in a ratio of 20 to 50% by weight on the basis of the total weight o,f the mixture of the water and organic solvent. The improved starch paste is prepared by treating a natural starch or an ~-starch with the organic solvent either before or after converting the starch into a starch paste.
The starches which can be used in the present invention are not limited to specific types and include potato starches, sweet potato starches, rice starches, wheat starches, corn starches, or the like, and the
101351~7 is provided in a wet granulating process for preparing granules having improved disintegration properties, the improvement which comprises using a starch paste binder prepared by admixing an organic solvent selected from the group consisting o~ acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereoE with a starch paste.
:, :
,.
.,.~ . .
- 2a -~8~0~
The invention inclu(les lmproved starcll pastes produced by tl~e process or method deEined a'bove, An advantage of the present lnvention, at least in the preferred forms, ls that it can provide an improved starch paste having good dislntegration proper-ties, which is therefore useful as a binder for gran~les.
~ nother advantage of the invention, at least in the preferred forms, that it can provide a method for improving the disintegration properties of conventional starch pastes.
A sti'll futher advantage of the invention is that it can provide improved granules for foodstuffs, medicines or the like.
These and other advantages of the inventLon will become apparent from the following description of the preferred embodiments of the invention.
The improved starch paste of the present invention comprises 5 to 20% by weight of a gelatinized starch and 95 to 80% by weight of a mixture of water and an organic solvent selected from alcohols having 1 to 3 ' carbon atoms, acetone and mi~tures thereof, wherein the organic solvent is contained in a ratio of 20 to 50% by weight on the basis of the total weight o,f the mixture of the water and organic solvent. The improved starch paste is prepared by treating a natural starch or an ~-starch with the organic solvent either before or after converting the starch into a starch paste.
The starches which can be used in the present invention are not limited to specific types and include potato starches, sweet potato starches, rice starches, wheat starches, corn starches, or the like, and the
- 3 -:.
5~7 starches used may l~e natural starches or ~-starches.
The organic solvents incLude alcohols having 1 to 3 carbon atoms (e.g. methyl alcohol, ethyl alcohol, propyl alcohol or lsopropyl alcohol) and acetone. These may be used alone or in admi~ttlre, Eor instance, a mix-ture of two or more alcohols or a mixture of one or more alcohols and acetone.
The improved starch paste can be prepared by treating a natural starch or an ~-starch with the organic solvent at any stage during the preparation of a starch paste from starch in the conventional manner, for ins-tance, (1) by dispersing a dried ~~starch into a mixture of water and the organic solvent, (2) by dispersing a natural starch in water, heating the resulting disper- --' sion until a paste is formed and then adding thereto the ; organic solvent, or (3) by dispersing a natural starch in a mixture of water and the organic solvent and heating the resulting dispersion until a paste is formed.
When a mixture of an alcohol and acetone is used as the organic solvent, there is usually no limita-; tion in the mixing ratio thereof, but when such a mixture is used in the above process (3), i.e. when the starch paste is prepared by dispersing the starch into a mixture ;; of water, an alcohol and acetone and heating the resulting dispersion, the mixing ratio of the alcohol and acetone should preferably be controlled so that the resulting dispersion has a boiling point of about 70C or higher.
The organic solvent is usually used in an amount of 20 to 50~ by weight on the basis of the total ; 30 weight of the water and the organic solvent. A suitable amount of the organic solvent can be determined by the :' - .
`:
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~0~35~L~37 color difference in a starch-io~l-ine reactlon which can be performed by flltering the supernatant ILqulcl Erom the starch paste and adding three drops of an iodine reagent to the filtrate (about 20 ml). That is, when the organic solvent is added to the mixture during the preparation of the starch paste , the color of the fil-trate in the starch-iodine reaction changes fro~ dark blue -~ bluish violet -~ violet ~ reddish violet -~ reddish brown ~ brown -~ yellowish brown -~ light yellow as the mixing ratio of the organic solvent increases. A suitable mixing ratio for the organic solvent is in the range that produces a violet to yellowish brown color of the filtrate in the starch-iodine reaction. For :instance, ; in case of a starch paste (100 parts by weight) containing a corn starch (5 to 15 parts by weight)g there is obtained a preferred product when an organic solvent (e.g. methanol) is used in an amount of 30 to 40% by weight on the basis of the total weight of the water and the organic solvent (e.g. methanol~.
In the starch paste of the present invention, the starch is used in an amount of 5 to 20% by weight on the basis of the total weight of the mixture of the water, organic solvent and starch, as in convent'iona:L processes for the preparation of starch pastes.
The improved starch paste of the present invention has good disintegration and binding properties and is useful as a binder for wet granulations, such as a wet milling granulation, extruding granulation, granu-~; lation by tumbling, fluidized bed granulation, spray drying granulation, or the like and can give an excellent gran~lar product. The paste can be used to form granules -:
.
~35~7 irl the conventiollaL way.
The granuLar products LncLucle fine and large granules. The granules may be forn~ed lnto tablets by compression or may be contained in capsules. The granu-lar products are usually soft and pleasant on the tongue and promptly disintegrate when dispersed in water or hot water. As a result, the granules are useful in various fields, such as foodstuffs, agriculturaL chemcials, fer-tilizers as well as medicines. ~or example, the granular products may be used in the field of foodstuffs as instan-taneously soluble products, such as in granulated juice or milk, or the ]ike.
The present invention is illustrated by the "
following Examples but is not limited thereto.
Example 1 ., .
A mixture of a corn starch (10 parts by weight) and a 35% by weight a~ueous methyl alcohol solution (90 parts by weight) was heated at about 76C
to give a starch paste. The starch paste thus obtained (about 730 g) was added to a mixture of lactose (1,400 g) and a corn starch (600 g), which were previously mixed in a kneader, and then the mixture was kneaded for about 10 minutes. The resulting mixture was subjected to a wet milling granulation and then dried at 50C for about 30 minutes with a fluidized bed dryer. The dried granules thus obtained were passed ~hrough a No. 12 (1,~10 ~) sieve ' : .
using an oscillator and then subiected to separation with a No. 24 t710 ~) sieve to give granules having a particle size distribution of 1,410 ~ to 710 ~. The granules thus obtained were subiected to a disintegration test by the method described in Pharmacopoeia of Japan (8~h edition), General Test, 31 Disintegration Test,(7) Granules. As ~:
: the result, the granules were disintegrated within one minute in good state to give fine particles which were . promptly dispersed. :~.
~; "
: 10 For comparison purpose, a starch paste was ~:
prepared by heating a mixture of a corn starch (10 :
, parts by weight) .:
.
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i107 and water (90 I)arts b,y weight) a-t rlbout 76C. The s-tarch paste thus obtained (about 560 g) ~I S kneaded together with a mixture of lactose ancl a corn starch, and the resulting mixture was subjec-ted to we-t gr.lnu:Ln-tion, drying, dry screen-ing and separation to give gr.lnulcs in the same manner as described above. The gran~Lles -thus ob-tai,ned were subjected to the disintegra-tion test as described above. As the result, the disintegration requires about 20 minutes, and the dis-integration behavior was not good and the granules are no-t di~integrated into fine particles and are not dispersed, but many coarse particles were remained in the beaker.
Example 2 A mixture of a wheat starch (:L0 parts by weight) ..
and a 45 7~ by weight a~ueous ethyl alcohol solution (90 parts by weight) was heated at about 78C to eive a s-tarch paste. The starch paste thus obtained (about 785 g) was added to a mixture of diazepam (7-chloro-1,~-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiaze~in-2-one, 20 g), a corn starch (~80 g) and lactose (1,600 g), which were previously ', 20 mixed in a kneader, and then the mixtllre was kneaded for '~ about 10 minutes. The resulting mixture was granula-ted withan extrusion type granula-tor provided with a screen having : a hole diameter.. of 0~8,~mm and then dried at 50C f'or slbOut 30 minutes with.a fluidized bed dryer. The dried granules thus obtained were passed through a No. 12 (1,410 ~) sieve , using an oscillator and then subjected to sep.lration ~ith a No.
'' 24 (710 ~) sieve to give granules having a particle size di.s-tribution of 1,410 ~ to 710 Il. The granules thus obtained were subjected to the disintegration test in the same manner as des-cribed in ~xample 1. As the result, the granules were disin-.
~ . ' . .
tegrated within one minute to give fine particles which were promptly dispersed.
For comparison purpose, a starch paste wa~ pre pared by heating a mixture of a wheat starch (10 parts by weight) and water (90 parts by weight) at about 78C. The starch paste thus obtained ~480 g) was added to the same mixture as described above, which was previously mixed in a kneader, and then the mixture was kneaded for about 10 minutes, and the resulting mixture was subjected to wet:
. :
; 10 granulation, drying, dry screening and separation to give granules in the same manner as described above. The granules thus obtained was subjected to the disintegration test like-i wise. As the result, the disintegration re~uire about 10 minutes, and the disintegration state was not good and coarse particles were remained in the beaker.
Example 3 A mixture of a potato starch (15 parts by weight) and a 35% by weight a~ueous isopropyl alcohol solution (85 parts by weight) was heated at about 78C to give a starch 20 paste. The starch paste thus obtained (about 860 g) was add- ;~
ed to a mixture of diazepam (20 g), a corn starch (380 g) and lactose (1,600 g), which were previously mixed with a kneader, and the mixture was kneaded for about 10 minutes. The result-ing mixture was subjected to a wet milling granulation with a No. 4 (4~760 ~) sieve and the granules thus obtained were dried at 50C for about 18 hours with a tray dryer. The dried granules were passed through a Nc. 12 (1,410 ~) sieve using ~`~
an oscillator and then subjected to separation with a No. 24 (710 ~) sieve to give granules having a particle size distri-30 bution of 1,410 ~ to 710 ~. The granules thus obtained were . , ~ ': "
~L~8~7 subjected to the disintegration test likewise. As the re-i:
sult, the granules were disintegrated within one minute in good state to give fine particles which ~were promptly dis-persed. Moreover, as is shown in Table 1, diazepam included i in the granules was dissolved well into ~water of 37C.
For comparison purpose, a starch paste was pre-pared by heating a mixture of a potato starch 115 parts by weight) and water (85 parts by weight) at about 72C. The starch paste thus obtained (475 g) was added to the same mixture as described above, which was previously mixed in a kneader, and the mixture is kneaded for about 10 minutes, and the resulting mixture was subjected to wet granulation, drying, dry screening and separation to give granules in the same manner as described above. The granules thus obtained were subjected to the disintegration test likewise. As the result, the disintegration required more than 30 minutes, ;~ which did not meet to the standard as defined in Pharmacopoeia ~- of Japan. Moreover, as is shown in Table 1, the dissolution - o diazepam was so inferior.
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~351~17 Table 1 Comparlson of dissolution rate of diazepam granules Granule Time for disso,lution (m,inu-te) 5 ~ ' 10 20 ' '30'~
. _ . _ invention 70 ~/o ¦ 93 ~ 100'~' 100 ~i' ~ . _ ., ,. . _ . .
P _ 25 ~o ~ 37 ~/o 51 ~0 62 ~0 .
[Reraark]: ~he di~solution -test was carried out hy the ,~ lo method as described in Pharmacopoeia of U.S;A.
(18th edition)~ (0.5 g of the sample in 1,000 ml of water, 37C, 100 rpm) xample 4 mixture of a corn staxch (65 part~ by weight) and water (585 parts by weight) was heated at 83C and there~
to was added ethyl alcohol (350 parts by weight), and the mix-ture was agitated well with an agitating stick to give a ' starch paste containing ethyl alcohol. The starch paste , ;
, thus obtained (620 g) was added to a mixture of lactose ~ -(1,400 g) and a corn starch (600 g), which were previously ~ ~' mixed in a kneader, and the mixture wa3 kneaded for about ~ 10 minutes. The resulting mixture was granulated with an `' '~ extrusion type granulator'provided withla screen having a -~
. . , hole diameter of 0.8 mm and then dried at 50~C ~or abou-t '~0 ;,'i,,~
minutes with a fluidized bed dryer. The dried granules thus ' , obtained ~ere subjected to separation with a sifter provided ~ , , '' with No, 12 (1,410 ~) and No. 24 (710 ~) sieves to give ~', granules having a particle size distribution of 1,410 ~ to 710 Il. The granules thus obtained were subjected to a dis- ~' .,' ~" 30 integration test by the method descrlbed in Pharmacopoeia ~ ~
'`;' ~: '`',' ~, (1 7 of Japan (8th edition), General Test, 31 Disintegration Test, (7) Granules. As the result, the gxanules were disintegrated within one minute to give f:ine particles which are promptly dispersed.
For comparison purpose, a starch paste was pre-pared by heating a mixture of a corn starch (65 parts by weight) and water (935 parts by weight3 at 83C. The starch paste thus obtained (565 g) was adcled to the same ~-~ mixture as above, which was previously mixed with a kneader, and the mixture was kneaded for about 10 minutes, and the resulting mixture was subjected to wet granulation, drying ~ and separation to give granules in the same manner as des-;~ cribed above. The granules thus obtained were subjected to the disintegration test in the same manner as described above. As the result, the disintegration required about 12 minutes, and khe disintegration behavior was not good and coarse particles were remained in the beaker.
Example 5 A mixture of a wheat starch (70 parts by weight) 20 and water (630 parts by weight) was heated ~t 80C and there-to was added methyl alcohol (300 parts by weight), and the mixture was agitated well with an agitating stick to give a starch paste containing methyl alcohol. The starch paste thus o~tained (580 g) was added to a mixture of lactose (1,500 g) and a corn starch (500 g), which were previously mixed in a kneader, and the mixture was kneaded for about 10 minutes.
The resulting mixture was granulated with an extrusion type granulator provided with a screen having a hole diameker of 0.~ mm and then dried at 50C for about 30 minutes with a fluidized bed dryer. The dried granules thus obtained were , 108~7 subjected to separation with a sifter provided with No. 16 (1,000 ~) and No~ 32 (500 ~) sieves to give granules having a particle size distribution of 1,000 to 500 ~. The gra-nules thus obtained are subjected to a disintegration test by the method described in Pharmacopoeia of Japan (8th edi tion), General Test, 31 Disintegration Test, (7) Granules.
As the result, the granules were disintegrated within one minute to give fine particles which were promptly dispersed.
For comparison purpose, a starch paste was prepared by heating a mixture of a wheat starch (70 parts by weight) and water (930 parts by weight) at 80C. The starch paste thus obtained (500 g) was added to the same mixture as above, which was previously kneaded with a kneader, and the mixture was kneaded for about 10 minutes, and the resulting mixture was subjected to granulation, drying and separation to give granules in the same manner as described above. The granules thus obtained were subjected to the disinteyr~tion test in ~-; the same manner as above. As the result, the disintegration ~ ;~
required about 10 minutes, and the disintegration behavior was not good and coarse particles were remained in the beaker.
Example 6 -. .
A mixture o~ a corn starch (105 parts by weight) and water ~595 parts by weight) was heated at 76C and there-to was added acetone (300 parts by weight), and the mixture is agitated well to give a starch paste. The starch paste thus obtained (600 g) was added to a mixture of lactose (1,960 g) and diazepam (40 g), which were previously mixed in a kneader, and the mixture was kneaded for about 10 minutes.
The resulting mixture was subjected to a wet milling granu~
lation with a No. 4 (4,760 ~) sieve and then dried at 50C for ~35~37 about 30 minutes with a fluidized bed dryer~ The dried gran~lles were passed through a No. 12 (1,410 ~) sieve using an oscillator and then subjected to separation with a No.
24 (710 ~I) sieve to give granules having a particle size distribution of 1,410 ~ to 710 ~. The granules thus obtained ( about 1 g) was added to a beaker which contains water of 22C (50 ml), when the beaker was lightly shaken, the gra-nules were promptly disintegrated to give fine particles which promptly dispersed.
For comparison purpose, a starch paste was prepared by heating a ~ixture of a corn starch (105 parts by weight) and water (895 parts by weight) at about 76C. The starch paste thus obtained (440 g) was kneaded together with a mix-ture of lactose and diazepam and then was subjected to wet granulation, drying, dry screening and separation to give gra-nules in the same manner as described above. The granules thus obtained were subjected to the disintegration test like-wise. As the result, the granules were not disintegrated into fine particles and were not dispersed, but many coarse parti-cles were remained in the bottom of the beaker Exam~le 7 To a mixture (90 parts by weight) of water (60 %
by weight), methyl alcohol (20 % by weight) and ethyl alcohol (20 % by weight) was added with agitation an a-corn starch ; (Amicol C - Trade Mark - a product of Nichiden Kagaku K.K., 10 parts by weight) to give a paste. The starch paste thus obtained (640 g) was added to a mixture of lactose (1,800 g), and precipitated calcium carbonate (200 g), which were previously mixed in a kneader, and the mixture was knead-ed for about 10 minutes. The resulting mixture was subjected .
. .
~ 14 -; :
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..
~01 3Si~07 to a wet milling granulation with a i~o. ~ (4,760 ~I) sieve and then dricd at 50C for about 30 rninutes with a fluidized bed dryer. The dried granules thus obtalned were passed tilrough a l~o. 12 (1,410 jl) sieve using an oscillator and -then subjected to separation with a No. ~4 (710 ~) sieve to give granules having a particle size distribution of 1,~10 ~ to 710 Il. 'l'he granules thus obtained (about 1 g) were added to a beaker which contains water of 22C (50 ml). ~en the beaker was lightly shaken, the granules were promptly disin~ ;
tegratèd to give fine particles which were promptly dispersed.
For comparison purpose, a starch paste was prepared by agitating a mixture of an a-corn starch (10 parts by weightj?
and water (90 parts by weight). The starch paste thus ob-tain-ed (440 ~g) was kneaded with a mlxture of lactose and precipit-ated cnlcium carbonate and then the rnixture was subjected to wet granulation, drying, dry screening and separation to give granules in the same rnanner as described above. The granules ~ thus obtained were subjected to the disintegration test like-; wise. As the resultl the granules were not disinte~rated into fine particles and were not dispersed, but coarse particles were remained at the bottom of the beaker. --~
Example 8 To a 40 % by weight aqueous ethyl alcohol so]ution (95 parts by weight) was added with agitation an a-po-tato starch (Amicol H, a trade name of the prcduct of Nichiden Kagaku K.K., 5 parts by weigh-t) to give a paste, The starch paste thus obtained (760 g) was added to a mix-ture of lactose (1,400 g) and a corn starch ~600 g), which were previously mixed in a kneader, and the mixture was l;neaded for about 10 minutes. The resul-ting mixture was subjected to a wet milling . ' ,.~
~ 15 ~
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. , :
granulation with a No. 4 (4,160 ~) sieve and then dried at 50C for about 5 hours with a tray dryer. The dried granules were passed throu~h a No. 12 (1,~10 Il) sieve using an oscilla-tor and then subjected -to separation with a No. 32 (500 ~I) sieve to ~ive granules hnving a particle size distribution of 1,410 ~1 to 500 ~I. The granules thus obtained (about 1 g) was added to a beaker which contains water of 22C (50 ml).
When the beaker was lightly shaken, the granules were prompt-ly disintegrated to give fine particles which were promptly lo dispersed.
For comparison purpose, a starch paste was pre-pared by agitating a mixture of an a-potato starch (5 parts by weight) and water (95 parts by ~eight). The starch paste thus obtained (430 g) was kneaded with a mixture of lactose ; and a corn starch, and then the mixture ~as subjected to wet i granulation, drying, dry screening and separation to give ~ranules in the same manner as described above. The granules -thus obtained were subjected to the disintegration test like-wise. As the resultj the granules were not disintegrated into 20 ~ine particles and were not dispersed, but coarse particles ~ -wsre remained at the bottom of the beaker.
',','. " , ~'''' :, :
.
'' ~; ' ;' .. ~ .
,; , ~ 30 ~ I!
., .
- ;
. . ,
5~7 starches used may l~e natural starches or ~-starches.
The organic solvents incLude alcohols having 1 to 3 carbon atoms (e.g. methyl alcohol, ethyl alcohol, propyl alcohol or lsopropyl alcohol) and acetone. These may be used alone or in admi~ttlre, Eor instance, a mix-ture of two or more alcohols or a mixture of one or more alcohols and acetone.
The improved starch paste can be prepared by treating a natural starch or an ~-starch with the organic solvent at any stage during the preparation of a starch paste from starch in the conventional manner, for ins-tance, (1) by dispersing a dried ~~starch into a mixture of water and the organic solvent, (2) by dispersing a natural starch in water, heating the resulting disper- --' sion until a paste is formed and then adding thereto the ; organic solvent, or (3) by dispersing a natural starch in a mixture of water and the organic solvent and heating the resulting dispersion until a paste is formed.
When a mixture of an alcohol and acetone is used as the organic solvent, there is usually no limita-; tion in the mixing ratio thereof, but when such a mixture is used in the above process (3), i.e. when the starch paste is prepared by dispersing the starch into a mixture ;; of water, an alcohol and acetone and heating the resulting dispersion, the mixing ratio of the alcohol and acetone should preferably be controlled so that the resulting dispersion has a boiling point of about 70C or higher.
The organic solvent is usually used in an amount of 20 to 50~ by weight on the basis of the total ; 30 weight of the water and the organic solvent. A suitable amount of the organic solvent can be determined by the :' - .
`:
: : , . .: .-- . .~ .
~0~35~L~37 color difference in a starch-io~l-ine reactlon which can be performed by flltering the supernatant ILqulcl Erom the starch paste and adding three drops of an iodine reagent to the filtrate (about 20 ml). That is, when the organic solvent is added to the mixture during the preparation of the starch paste , the color of the fil-trate in the starch-iodine reaction changes fro~ dark blue -~ bluish violet -~ violet ~ reddish violet -~ reddish brown ~ brown -~ yellowish brown -~ light yellow as the mixing ratio of the organic solvent increases. A suitable mixing ratio for the organic solvent is in the range that produces a violet to yellowish brown color of the filtrate in the starch-iodine reaction. For :instance, ; in case of a starch paste (100 parts by weight) containing a corn starch (5 to 15 parts by weight)g there is obtained a preferred product when an organic solvent (e.g. methanol) is used in an amount of 30 to 40% by weight on the basis of the total weight of the water and the organic solvent (e.g. methanol~.
In the starch paste of the present invention, the starch is used in an amount of 5 to 20% by weight on the basis of the total weight of the mixture of the water, organic solvent and starch, as in convent'iona:L processes for the preparation of starch pastes.
The improved starch paste of the present invention has good disintegration and binding properties and is useful as a binder for wet granulations, such as a wet milling granulation, extruding granulation, granu-~; lation by tumbling, fluidized bed granulation, spray drying granulation, or the like and can give an excellent gran~lar product. The paste can be used to form granules -:
.
~35~7 irl the conventiollaL way.
The granuLar products LncLucle fine and large granules. The granules may be forn~ed lnto tablets by compression or may be contained in capsules. The granu-lar products are usually soft and pleasant on the tongue and promptly disintegrate when dispersed in water or hot water. As a result, the granules are useful in various fields, such as foodstuffs, agriculturaL chemcials, fer-tilizers as well as medicines. ~or example, the granular products may be used in the field of foodstuffs as instan-taneously soluble products, such as in granulated juice or milk, or the ]ike.
The present invention is illustrated by the "
following Examples but is not limited thereto.
Example 1 ., .
A mixture of a corn starch (10 parts by weight) and a 35% by weight a~ueous methyl alcohol solution (90 parts by weight) was heated at about 76C
to give a starch paste. The starch paste thus obtained (about 730 g) was added to a mixture of lactose (1,400 g) and a corn starch (600 g), which were previously mixed in a kneader, and then the mixture was kneaded for about 10 minutes. The resulting mixture was subjected to a wet milling granulation and then dried at 50C for about 30 minutes with a fluidized bed dryer. The dried granules thus obtained were passed ~hrough a No. 12 (1,~10 ~) sieve ' : .
using an oscillator and then subiected to separation with a No. 24 t710 ~) sieve to give granules having a particle size distribution of 1,410 ~ to 710 ~. The granules thus obtained were subiected to a disintegration test by the method described in Pharmacopoeia of Japan (8~h edition), General Test, 31 Disintegration Test,(7) Granules. As ~:
: the result, the granules were disintegrated within one minute in good state to give fine particles which were . promptly dispersed. :~.
~; "
: 10 For comparison purpose, a starch paste was ~:
prepared by heating a mixture of a corn starch (10 :
, parts by weight) .:
.
:, ~' ' , "'' ,, .: ~ ~ :
.,, '' ":;
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, ~ - . . , ' :. :' ,,. . : ' . ' ' :
i107 and water (90 I)arts b,y weight) a-t rlbout 76C. The s-tarch paste thus obtained (about 560 g) ~I S kneaded together with a mixture of lactose ancl a corn starch, and the resulting mixture was subjec-ted to we-t gr.lnu:Ln-tion, drying, dry screen-ing and separation to give gr.lnulcs in the same manner as described above. The gran~Lles -thus ob-tai,ned were subjected to the disintegra-tion test as described above. As the result, the disintegration requires about 20 minutes, and the dis-integration behavior was not good and the granules are no-t di~integrated into fine particles and are not dispersed, but many coarse particles were remained in the beaker.
Example 2 A mixture of a wheat starch (:L0 parts by weight) ..
and a 45 7~ by weight a~ueous ethyl alcohol solution (90 parts by weight) was heated at about 78C to eive a s-tarch paste. The starch paste thus obtained (about 785 g) was added to a mixture of diazepam (7-chloro-1,~-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiaze~in-2-one, 20 g), a corn starch (~80 g) and lactose (1,600 g), which were previously ', 20 mixed in a kneader, and then the mixtllre was kneaded for '~ about 10 minutes. The resulting mixture was granula-ted withan extrusion type granula-tor provided with a screen having : a hole diameter.. of 0~8,~mm and then dried at 50C f'or slbOut 30 minutes with.a fluidized bed dryer. The dried granules thus obtained were passed through a No. 12 (1,410 ~) sieve , using an oscillator and then subjected to sep.lration ~ith a No.
'' 24 (710 ~) sieve to give granules having a particle size di.s-tribution of 1,410 ~ to 710 Il. The granules thus obtained were subjected to the disintegration test in the same manner as des-cribed in ~xample 1. As the result, the granules were disin-.
~ . ' . .
tegrated within one minute to give fine particles which were promptly dispersed.
For comparison purpose, a starch paste wa~ pre pared by heating a mixture of a wheat starch (10 parts by weight) and water (90 parts by weight) at about 78C. The starch paste thus obtained ~480 g) was added to the same mixture as described above, which was previously mixed in a kneader, and then the mixture was kneaded for about 10 minutes, and the resulting mixture was subjected to wet:
. :
; 10 granulation, drying, dry screening and separation to give granules in the same manner as described above. The granules thus obtained was subjected to the disintegration test like-i wise. As the result, the disintegration re~uire about 10 minutes, and the disintegration state was not good and coarse particles were remained in the beaker.
Example 3 A mixture of a potato starch (15 parts by weight) and a 35% by weight a~ueous isopropyl alcohol solution (85 parts by weight) was heated at about 78C to give a starch 20 paste. The starch paste thus obtained (about 860 g) was add- ;~
ed to a mixture of diazepam (20 g), a corn starch (380 g) and lactose (1,600 g), which were previously mixed with a kneader, and the mixture was kneaded for about 10 minutes. The result-ing mixture was subjected to a wet milling granulation with a No. 4 (4~760 ~) sieve and the granules thus obtained were dried at 50C for about 18 hours with a tray dryer. The dried granules were passed through a Nc. 12 (1,410 ~) sieve using ~`~
an oscillator and then subjected to separation with a No. 24 (710 ~) sieve to give granules having a particle size distri-30 bution of 1,410 ~ to 710 ~. The granules thus obtained were . , ~ ': "
~L~8~7 subjected to the disintegration test likewise. As the re-i:
sult, the granules were disintegrated within one minute in good state to give fine particles which ~were promptly dis-persed. Moreover, as is shown in Table 1, diazepam included i in the granules was dissolved well into ~water of 37C.
For comparison purpose, a starch paste was pre-pared by heating a mixture of a potato starch 115 parts by weight) and water (85 parts by weight) at about 72C. The starch paste thus obtained (475 g) was added to the same mixture as described above, which was previously mixed in a kneader, and the mixture is kneaded for about 10 minutes, and the resulting mixture was subjected to wet granulation, drying, dry screening and separation to give granules in the same manner as described above. The granules thus obtained were subjected to the disintegration test likewise. As the result, the disintegration required more than 30 minutes, ;~ which did not meet to the standard as defined in Pharmacopoeia ~- of Japan. Moreover, as is shown in Table 1, the dissolution - o diazepam was so inferior.
:,, ' ,~
" ' ,:
:- .
~351~17 Table 1 Comparlson of dissolution rate of diazepam granules Granule Time for disso,lution (m,inu-te) 5 ~ ' 10 20 ' '30'~
. _ . _ invention 70 ~/o ¦ 93 ~ 100'~' 100 ~i' ~ . _ ., ,. . _ . .
P _ 25 ~o ~ 37 ~/o 51 ~0 62 ~0 .
[Reraark]: ~he di~solution -test was carried out hy the ,~ lo method as described in Pharmacopoeia of U.S;A.
(18th edition)~ (0.5 g of the sample in 1,000 ml of water, 37C, 100 rpm) xample 4 mixture of a corn staxch (65 part~ by weight) and water (585 parts by weight) was heated at 83C and there~
to was added ethyl alcohol (350 parts by weight), and the mix-ture was agitated well with an agitating stick to give a ' starch paste containing ethyl alcohol. The starch paste , ;
, thus obtained (620 g) was added to a mixture of lactose ~ -(1,400 g) and a corn starch (600 g), which were previously ~ ~' mixed in a kneader, and the mixture wa3 kneaded for about ~ 10 minutes. The resulting mixture was granulated with an `' '~ extrusion type granulator'provided withla screen having a -~
. . , hole diameter of 0.8 mm and then dried at 50~C ~or abou-t '~0 ;,'i,,~
minutes with a fluidized bed dryer. The dried granules thus ' , obtained ~ere subjected to separation with a sifter provided ~ , , '' with No, 12 (1,410 ~) and No. 24 (710 ~) sieves to give ~', granules having a particle size distribution of 1,410 ~ to 710 Il. The granules thus obtained were subjected to a dis- ~' .,' ~" 30 integration test by the method descrlbed in Pharmacopoeia ~ ~
'`;' ~: '`',' ~, (1 7 of Japan (8th edition), General Test, 31 Disintegration Test, (7) Granules. As the result, the gxanules were disintegrated within one minute to give f:ine particles which are promptly dispersed.
For comparison purpose, a starch paste was pre-pared by heating a mixture of a corn starch (65 parts by weight) and water (935 parts by weight3 at 83C. The starch paste thus obtained (565 g) was adcled to the same ~-~ mixture as above, which was previously mixed with a kneader, and the mixture was kneaded for about 10 minutes, and the resulting mixture was subjected to wet granulation, drying ~ and separation to give granules in the same manner as des-;~ cribed above. The granules thus obtained were subjected to the disintegration test in the same manner as described above. As the result, the disintegration required about 12 minutes, and khe disintegration behavior was not good and coarse particles were remained in the beaker.
Example 5 A mixture of a wheat starch (70 parts by weight) 20 and water (630 parts by weight) was heated ~t 80C and there-to was added methyl alcohol (300 parts by weight), and the mixture was agitated well with an agitating stick to give a starch paste containing methyl alcohol. The starch paste thus o~tained (580 g) was added to a mixture of lactose (1,500 g) and a corn starch (500 g), which were previously mixed in a kneader, and the mixture was kneaded for about 10 minutes.
The resulting mixture was granulated with an extrusion type granulator provided with a screen having a hole diameker of 0.~ mm and then dried at 50C for about 30 minutes with a fluidized bed dryer. The dried granules thus obtained were , 108~7 subjected to separation with a sifter provided with No. 16 (1,000 ~) and No~ 32 (500 ~) sieves to give granules having a particle size distribution of 1,000 to 500 ~. The gra-nules thus obtained are subjected to a disintegration test by the method described in Pharmacopoeia of Japan (8th edi tion), General Test, 31 Disintegration Test, (7) Granules.
As the result, the granules were disintegrated within one minute to give fine particles which were promptly dispersed.
For comparison purpose, a starch paste was prepared by heating a mixture of a wheat starch (70 parts by weight) and water (930 parts by weight) at 80C. The starch paste thus obtained (500 g) was added to the same mixture as above, which was previously kneaded with a kneader, and the mixture was kneaded for about 10 minutes, and the resulting mixture was subjected to granulation, drying and separation to give granules in the same manner as described above. The granules thus obtained were subjected to the disinteyr~tion test in ~-; the same manner as above. As the result, the disintegration ~ ;~
required about 10 minutes, and the disintegration behavior was not good and coarse particles were remained in the beaker.
Example 6 -. .
A mixture o~ a corn starch (105 parts by weight) and water ~595 parts by weight) was heated at 76C and there-to was added acetone (300 parts by weight), and the mixture is agitated well to give a starch paste. The starch paste thus obtained (600 g) was added to a mixture of lactose (1,960 g) and diazepam (40 g), which were previously mixed in a kneader, and the mixture was kneaded for about 10 minutes.
The resulting mixture was subjected to a wet milling granu~
lation with a No. 4 (4,760 ~) sieve and then dried at 50C for ~35~37 about 30 minutes with a fluidized bed dryer~ The dried gran~lles were passed through a No. 12 (1,410 ~) sieve using an oscillator and then subjected to separation with a No.
24 (710 ~I) sieve to give granules having a particle size distribution of 1,410 ~ to 710 ~. The granules thus obtained ( about 1 g) was added to a beaker which contains water of 22C (50 ml), when the beaker was lightly shaken, the gra-nules were promptly disintegrated to give fine particles which promptly dispersed.
For comparison purpose, a starch paste was prepared by heating a ~ixture of a corn starch (105 parts by weight) and water (895 parts by weight) at about 76C. The starch paste thus obtained (440 g) was kneaded together with a mix-ture of lactose and diazepam and then was subjected to wet granulation, drying, dry screening and separation to give gra-nules in the same manner as described above. The granules thus obtained were subjected to the disintegration test like-wise. As the result, the granules were not disintegrated into fine particles and were not dispersed, but many coarse parti-cles were remained in the bottom of the beaker Exam~le 7 To a mixture (90 parts by weight) of water (60 %
by weight), methyl alcohol (20 % by weight) and ethyl alcohol (20 % by weight) was added with agitation an a-corn starch ; (Amicol C - Trade Mark - a product of Nichiden Kagaku K.K., 10 parts by weight) to give a paste. The starch paste thus obtained (640 g) was added to a mixture of lactose (1,800 g), and precipitated calcium carbonate (200 g), which were previously mixed in a kneader, and the mixture was knead-ed for about 10 minutes. The resulting mixture was subjected .
. .
~ 14 -; :
.. ..
..
~01 3Si~07 to a wet milling granulation with a i~o. ~ (4,760 ~I) sieve and then dricd at 50C for about 30 rninutes with a fluidized bed dryer. The dried granules thus obtalned were passed tilrough a l~o. 12 (1,410 jl) sieve using an oscillator and -then subjected to separation with a No. ~4 (710 ~) sieve to give granules having a particle size distribution of 1,~10 ~ to 710 Il. 'l'he granules thus obtained (about 1 g) were added to a beaker which contains water of 22C (50 ml). ~en the beaker was lightly shaken, the granules were promptly disin~ ;
tegratèd to give fine particles which were promptly dispersed.
For comparison purpose, a starch paste was prepared by agitating a mixture of an a-corn starch (10 parts by weightj?
and water (90 parts by weight). The starch paste thus ob-tain-ed (440 ~g) was kneaded with a mlxture of lactose and precipit-ated cnlcium carbonate and then the rnixture was subjected to wet granulation, drying, dry screening and separation to give granules in the same rnanner as described above. The granules ~ thus obtained were subjected to the disintegration test like-; wise. As the resultl the granules were not disinte~rated into fine particles and were not dispersed, but coarse particles were remained at the bottom of the beaker. --~
Example 8 To a 40 % by weight aqueous ethyl alcohol so]ution (95 parts by weight) was added with agitation an a-po-tato starch (Amicol H, a trade name of the prcduct of Nichiden Kagaku K.K., 5 parts by weigh-t) to give a paste, The starch paste thus obtained (760 g) was added to a mix-ture of lactose (1,400 g) and a corn starch ~600 g), which were previously mixed in a kneader, and the mixture was l;neaded for about 10 minutes. The resul-ting mixture was subjected to a wet milling . ' ,.~
~ 15 ~
' ~ ' ,.
. , :
granulation with a No. 4 (4,160 ~) sieve and then dried at 50C for about 5 hours with a tray dryer. The dried granules were passed throu~h a No. 12 (1,~10 Il) sieve using an oscilla-tor and then subjected -to separation with a No. 32 (500 ~I) sieve to ~ive granules hnving a particle size distribution of 1,410 ~1 to 500 ~I. The granules thus obtained (about 1 g) was added to a beaker which contains water of 22C (50 ml).
When the beaker was lightly shaken, the granules were prompt-ly disintegrated to give fine particles which were promptly lo dispersed.
For comparison purpose, a starch paste was pre-pared by agitating a mixture of an a-potato starch (5 parts by weight) and water (95 parts by ~eight). The starch paste thus obtained (430 g) was kneaded with a mixture of lactose ; and a corn starch, and then the mixture ~as subjected to wet i granulation, drying, dry screening and separation to give ~ranules in the same manner as described above. The granules -thus obtained were subjected to the disintegration test like-wise. As the resultj the granules were not disintegrated into 20 ~ine particles and were not dispersed, but coarse particles ~ -wsre remained at the bottom of the beaker.
',','. " , ~'''' :, :
.
'' ~; ' ;' .. ~ .
,; , ~ 30 ~ I!
., .
- ;
. . ,
Claims (2)
1. A process for preparing granules having improved disintegration properties, which comprises mixing materials to be granulated with a starch paste comprising 5 to 20 % by weight of a gelatinized starch and 95 to 80 %
by weight of a mixture of water and an organic solvent selected from the group consisting of acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereof wherein said organic solvent is present in a ratio of 20 to 50 % by weight based on the whole weight of the mixture of the water and the organic solvent, and then granulating the resulting mixture by a wet granulating process.
by weight of a mixture of water and an organic solvent selected from the group consisting of acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereof wherein said organic solvent is present in a ratio of 20 to 50 % by weight based on the whole weight of the mixture of the water and the organic solvent, and then granulating the resulting mixture by a wet granulating process.
2. In a wet granulating process for preparing granules having improved disintegration properties, the improvement which comprises using a starch paste binder prepared by admixing an organic solvent selected from the group con-sisting of acetone and an alcohol having 1 to 3 carbon atoms and a mixture thereof with a starch paste.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50074094A JPS5950375B2 (en) | 1975-06-17 | 1975-06-17 | Granule manufacturing method |
| JP74094/1975 | 1975-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085107A true CA1085107A (en) | 1980-09-09 |
Family
ID=13537244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,115A Expired CA1085107A (en) | 1975-06-17 | 1976-06-17 | Starch paste |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5950375B2 (en) |
| CA (1) | CA1085107A (en) |
| DE (1) | DE2627122A1 (en) |
| FR (1) | FR2316331A1 (en) |
| GB (1) | GB1543750A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5091201A (en) * | 1989-04-05 | 1992-02-25 | Kanebo, Ltd. | Process for manufacturing molded food |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6240278A (en) * | 1985-08-15 | 1987-02-21 | Meiji Seika Kaisha Ltd | Production of granule of moisture-absorbing powder |
| US5051133A (en) * | 1988-12-12 | 1991-09-24 | Suntory Limited | Gelatinized cereal flours and process for their production |
| JPH02252413A (en) * | 1989-03-27 | 1990-10-11 | Honda Electron Co Ltd | Temperature-keeping article |
| GB9917339D0 (en) * | 1999-07-24 | 1999-09-22 | Cerestar Holding Bv | Starch granulation |
-
1975
- 1975-06-17 JP JP50074094A patent/JPS5950375B2/en not_active Expired
-
1976
- 1976-06-16 GB GB24945/76A patent/GB1543750A/en not_active Expired
- 1976-06-16 DE DE19762627122 patent/DE2627122A1/en not_active Withdrawn
- 1976-06-17 FR FR7618471A patent/FR2316331A1/en active Granted
- 1976-06-17 CA CA255,115A patent/CA1085107A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5091201A (en) * | 1989-04-05 | 1992-02-25 | Kanebo, Ltd. | Process for manufacturing molded food |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1543750A (en) | 1979-04-04 |
| JPS51149178A (en) | 1976-12-21 |
| DE2627122A1 (en) | 1976-12-30 |
| FR2316331A1 (en) | 1977-01-28 |
| JPS5950375B2 (en) | 1984-12-07 |
| FR2316331B1 (en) | 1980-11-21 |
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