CA1049334A - Process for coating water soluble or water dispersible particles by means of the fluid bed technique - Google Patents
Process for coating water soluble or water dispersible particles by means of the fluid bed techniqueInfo
- Publication number
- CA1049334A CA1049334A CA205,367A CA205367A CA1049334A CA 1049334 A CA1049334 A CA 1049334A CA 205367 A CA205367 A CA 205367A CA 1049334 A CA1049334 A CA 1049334A
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- CA
- Canada
- Prior art keywords
- coating
- particles
- water soluble
- water
- coated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/38—Products with no well-defined composition, e.g. natural products
- C11D3/386—Preparations containing enzymes, e.g. protease or amylase
- C11D3/38672—Granulated or coated enzymes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
- B01J2/006—Coating of the granules without description of the process or the device by which the granules are obtained
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/1872—Details of the fluidised bed reactor
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Combustion & Propulsion (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Detergent Compositions (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Paints Or Removers (AREA)
Abstract
ABSTRACT OF INVENTION
A process for coating water soluble or water dispersable particles by means of the fluid bed technique, comprising introduction of the particles to be coated in the fluid bed reactor and introduction of a coating fluid essentially consisting of an aqueous or substantially aqueous solution or dispersion of a macro-molecular film forming, water soluble or water dispersable coating agent by means of atomization, whereby the relative humidity of the outlet air is below 100%, and whereby the maximum size of the atomized droplets of the coating fluid does not exceed the minimum size of the particles to be coated, as well as the coated product prepared by the process.
A process for coating water soluble or water dispersable particles by means of the fluid bed technique, comprising introduction of the particles to be coated in the fluid bed reactor and introduction of a coating fluid essentially consisting of an aqueous or substantially aqueous solution or dispersion of a macro-molecular film forming, water soluble or water dispersable coating agent by means of atomization, whereby the relative humidity of the outlet air is below 100%, and whereby the maximum size of the atomized droplets of the coating fluid does not exceed the minimum size of the particles to be coated, as well as the coated product prepared by the process.
Description
~049334 This invention relates to a process for coating water soluble or water dispersible particles by means of the fluid bed technique.
It is known to coat various particulate products having a particle size of less than about 10 mm, preferably less than 1 mm, in order to minimize dust formation, e.g. enzyme containing additives for detergent compositions in powder form. I-Iowever, considerable difficulties have been experienced in performing this coating. In practice it has hitherto been usual to utilize coating agents dissolved in organic solvents rather than in water when coating water soluble particles. The organic solvents have to be evaporated and recovered at a later stage of the process and may, furthermore, create a fire hazard and environmental problems. If, on the other hand, the organic solvent is not recovered, the coating process works in an uneconomical way~ ~ ~
Also, it is known to utilize the fluid bed technique to ~ -coat various water soluble or water dispersible particles by atomization of aqueous solutions of film forming, water soluble coating agents, this process being described in Wurster's USA
patent No. 3,196,827. However, in this known process it is difficult to avoid agglomeration of the particles to be coated, and it is mentioned that this known process is only suited for particles bigger than 30 mesh (ab. 0.6 mm). Also, by using Wurster's method it is difficult to obtain thin coatings.
~ We have now found that it is possible to utilize an ; aqueous or substantially aqueous liquid for coating particulate products having a particle size of less than about 1 mm in a fluid bed process whereby particles can be coated with an extremely thin coating and without substantial danger of agglomeration.
More specifically, the process of the invention for coating water soluble or water dispersible particles by means A~ .
~ ' of the fluid be~ technique comprises introdllcing the particles to be coated in a fluid bed reactor, the mean diameter of the particles to be coated being in the ran~e of from 0.1 to 0.6 mm, and introducing a coating fluid essentially consisting of an aqueous or substantially aqueous solution or dispersion of a macromolecular film forming, water soluble or water dispersible coating agent by means of atomization, wherein the relative humi-dity of the outlet air from the fluid bed reactor is below 100% and wherein the maxirnum size of the atomized droplets of the coating fluid does not exceed the minimum size of the particles ~ be coated.
The invention also relates to a coated product which has a core of active substance formed particles having a diameter of 0.1 - 0.6 mm, which core has a thin coating of a macromolecular film forming substance.
If the maximum size of the atomized droplets of the coating fluid exceeds the minimum size of the particles to be coated, agglomeration will occur.
m us, by means of the invention agglomeration can be avoided, and it is possible to perform the coating with a layer 20 as thin as about 0.1 - 10 ~, in a preferred embodiment 0.5 corresponding to about 1% of the dry particle weight. For a given thickness of the layer of coating agent a larger amount of coating agent, calculated on the particle weight, will be used with decreasing particle size. This will appear from the following Table I.
TABLE I
Amount of coating agent, calculated as percent by weight of the particles to be coated ALCALASE P * ALCALAS E M *
Thickness of Mean diameter of Mean diameter of coatinq particles 400 ~ partic _s 700 0.5 ~ 0.8 % 0.5 %
1.0 ~ 1.5 % 0.9 %
* trademark B` - -2-~ lthough the coating produced according to the invention in a preferred embodiment is very thin it is, according to the invention, also possible to produce coatings as thick as about 100 ~, if desired The minimum size of the particles to be coated can be determined by sieve analysis, and the maximum size of the atomized droplets of coating fluid can be read from charts available from the manufacturer of the nozzle, when the viscosity of the fluid and the pressure is known.
In a preferred embodiment of the process according to the invention the water soluble or water dispersible particles to be coated contain one or more enzymes as an active ingredient, e.g. proteases, amylases, lipases or celluloses.
In another preferred embodiment of the process according to the invention the enzyme or enzymes are bacterial proteinases.
In another preferred embodiment of the process according to the invention the bacterial proteinases are precoated in order to reduce dust formation.
In another preferred embodiment of the process according to the invention the bacterial proteinases are ALCALASE P or ALCALASE M.
ALCALASE, which is a trade mark belonging to NOVO
INDUSTRI A/S, is a microbial proteinase. ALCALASE P is a prilled ALCALASE. ALCALASE M is ALCALASE which is treated by means of a Marumerizer as described in our British Patent No. 1,362,365, issued on December 4, 1974, and in our published French Patent No. 2,099,349.
In another preferred embodiment of the process according to the invention the enzyme or enzymes are bacterial or fungal carbohydrases.
_3_ In another preferred embodiment of the process according to the invention the bacterial amylases are thermally stable amylases manufactured according to sritish Patent No. 1,296,839.
In another preferred embodiment of the process according to the invention the macromolecular film forming, water soluble or water dispersible coating agent is a cellulose derivative.
In another preferred embodiment of the process according to the invention the cellulose derivative is methyl cellulose, hydroxybutylmethyl cellulose, sodium carboxymethyl cellulose, hydroxyethylmethyl cellulose or hydroxypropylmethyl cellulose.
In another preferred embodiment of the process according to the invention the macromolecular film forming, water soluble or water dispersible coating agent is a polyvinylpyrrolidone.
104g334 ~ n another preferred embodiment of the process according to the in~ention t~le macromolecular film forming, water soluble or water dispersable coating agent is a polyethylene glycol~
preferably of a molecular weight of between about 400 and about 6000.
In another preferred embodiment of the process according to the invention the macromolecular film formingJ water soluble or water dispersable coating agent is a methacrylic resin.
In another preferred embodiment of the process according to the invention the macromolecular film forming, water soluble or water dispersable coating agent is gelatine.
In another preferred embodiment of the process according to the invention the coating fluid contains a-plasticizer.
In another preferred embodiment of the`process according to the invention the plasticizer is a glycerol.
In another preferred embodiment of the process according to the invention the glycerol is used in an amount of up to 60 % of the dry weight of the coating agent, preferably in an amount of between 10 and ~0 % of the dry weight of the coating agent.
In another preferred embodiment of the process according to the invention the concentration of the macromolecular film forming, water soluble or water dispersable coating agent in the coating fluid is between 2 and 50 weight-%.
In another preferre'd embodiment of the process according to the invention the concentration of the macromolecular film forming, water soluble or water dispersable coating agent in the coating fluid is between 4 and 10 weight-%.
In another preferred embodiment of the process according to the invention the mean diameter of the particles to be coated is between 0.1 and o.6 mm.
In another preferred embodiment of the process according to the invention the mean diameter of the particles to be coated is between 0.2 and o.6 mm.
1~4~334 1ll anot~le~ p~eferred em'~o~imerlt of tile p~ocess according to the invention the thlckness o~ the coating layer is be~ween 0.1 and 10 ~.
In another preferred embodiment o~ the process-according to the invention ~he thickness of the coating layer is between 0.5 and 1 ~. -The process according to the invention can be carried outin a continuous manner as well as batchwise. However, in a pre-ferred embodiment of the invention the process is carried out batchwise. In all the following examples the process is~ carried out batchwise.
The invention also encompasses a coated product comprising coated water soluble or water dispersable particles, whenever prepared by means of the process according to the invention.
The water soluble or water dispersable particles can be of any material which, for any reason, is to be coated. Examples of materials encompassed are enzyme additives, e.g. proteolytic enzyme additives for detergents, medicaments in pellet form, e.g.
oral penicillin preparations or hygroscopic substances, e.g.
fertilizers.
Coating of the particles is carried out for various reasons, e.g. in order to minimize dust formation, to protect against ultra-violet radiation, humidity or acidity, to minimize contamination, and the like.
The coating agent can be any macromolecular film forming, water soluble or water dispersable coating agent, e.g.
METHOCEL ~ MC 15: methyl cellulose of a methoxyl DS (Degree of Substitution) of 1.64 to 1.92 and o~ a DP (Degree of Poly-merization) corresponding to viscosities from 8 cP to 10,000 cP
in a 2 % aqueous solution at 20C.
TYLOSE ~ C 10: sodium carboxymethyl cellulose of a DS from 0.4 to 1.5 and a DP from 50 to 1000.
_ . ' , 10~9334 TYLoS~ 20: methylhydroxyeth~l cellulose (or hydroxyethylmethyl cellulose) of a methoxyl DS from 1.0 to
It is known to coat various particulate products having a particle size of less than about 10 mm, preferably less than 1 mm, in order to minimize dust formation, e.g. enzyme containing additives for detergent compositions in powder form. I-Iowever, considerable difficulties have been experienced in performing this coating. In practice it has hitherto been usual to utilize coating agents dissolved in organic solvents rather than in water when coating water soluble particles. The organic solvents have to be evaporated and recovered at a later stage of the process and may, furthermore, create a fire hazard and environmental problems. If, on the other hand, the organic solvent is not recovered, the coating process works in an uneconomical way~ ~ ~
Also, it is known to utilize the fluid bed technique to ~ -coat various water soluble or water dispersible particles by atomization of aqueous solutions of film forming, water soluble coating agents, this process being described in Wurster's USA
patent No. 3,196,827. However, in this known process it is difficult to avoid agglomeration of the particles to be coated, and it is mentioned that this known process is only suited for particles bigger than 30 mesh (ab. 0.6 mm). Also, by using Wurster's method it is difficult to obtain thin coatings.
~ We have now found that it is possible to utilize an ; aqueous or substantially aqueous liquid for coating particulate products having a particle size of less than about 1 mm in a fluid bed process whereby particles can be coated with an extremely thin coating and without substantial danger of agglomeration.
More specifically, the process of the invention for coating water soluble or water dispersible particles by means A~ .
~ ' of the fluid be~ technique comprises introdllcing the particles to be coated in a fluid bed reactor, the mean diameter of the particles to be coated being in the ran~e of from 0.1 to 0.6 mm, and introducing a coating fluid essentially consisting of an aqueous or substantially aqueous solution or dispersion of a macromolecular film forming, water soluble or water dispersible coating agent by means of atomization, wherein the relative humi-dity of the outlet air from the fluid bed reactor is below 100% and wherein the maxirnum size of the atomized droplets of the coating fluid does not exceed the minimum size of the particles ~ be coated.
The invention also relates to a coated product which has a core of active substance formed particles having a diameter of 0.1 - 0.6 mm, which core has a thin coating of a macromolecular film forming substance.
If the maximum size of the atomized droplets of the coating fluid exceeds the minimum size of the particles to be coated, agglomeration will occur.
m us, by means of the invention agglomeration can be avoided, and it is possible to perform the coating with a layer 20 as thin as about 0.1 - 10 ~, in a preferred embodiment 0.5 corresponding to about 1% of the dry particle weight. For a given thickness of the layer of coating agent a larger amount of coating agent, calculated on the particle weight, will be used with decreasing particle size. This will appear from the following Table I.
TABLE I
Amount of coating agent, calculated as percent by weight of the particles to be coated ALCALASE P * ALCALAS E M *
Thickness of Mean diameter of Mean diameter of coatinq particles 400 ~ partic _s 700 0.5 ~ 0.8 % 0.5 %
1.0 ~ 1.5 % 0.9 %
* trademark B` - -2-~ lthough the coating produced according to the invention in a preferred embodiment is very thin it is, according to the invention, also possible to produce coatings as thick as about 100 ~, if desired The minimum size of the particles to be coated can be determined by sieve analysis, and the maximum size of the atomized droplets of coating fluid can be read from charts available from the manufacturer of the nozzle, when the viscosity of the fluid and the pressure is known.
In a preferred embodiment of the process according to the invention the water soluble or water dispersible particles to be coated contain one or more enzymes as an active ingredient, e.g. proteases, amylases, lipases or celluloses.
In another preferred embodiment of the process according to the invention the enzyme or enzymes are bacterial proteinases.
In another preferred embodiment of the process according to the invention the bacterial proteinases are precoated in order to reduce dust formation.
In another preferred embodiment of the process according to the invention the bacterial proteinases are ALCALASE P or ALCALASE M.
ALCALASE, which is a trade mark belonging to NOVO
INDUSTRI A/S, is a microbial proteinase. ALCALASE P is a prilled ALCALASE. ALCALASE M is ALCALASE which is treated by means of a Marumerizer as described in our British Patent No. 1,362,365, issued on December 4, 1974, and in our published French Patent No. 2,099,349.
In another preferred embodiment of the process according to the invention the enzyme or enzymes are bacterial or fungal carbohydrases.
_3_ In another preferred embodiment of the process according to the invention the bacterial amylases are thermally stable amylases manufactured according to sritish Patent No. 1,296,839.
In another preferred embodiment of the process according to the invention the macromolecular film forming, water soluble or water dispersible coating agent is a cellulose derivative.
In another preferred embodiment of the process according to the invention the cellulose derivative is methyl cellulose, hydroxybutylmethyl cellulose, sodium carboxymethyl cellulose, hydroxyethylmethyl cellulose or hydroxypropylmethyl cellulose.
In another preferred embodiment of the process according to the invention the macromolecular film forming, water soluble or water dispersible coating agent is a polyvinylpyrrolidone.
104g334 ~ n another preferred embodiment of the process according to the in~ention t~le macromolecular film forming, water soluble or water dispersable coating agent is a polyethylene glycol~
preferably of a molecular weight of between about 400 and about 6000.
In another preferred embodiment of the process according to the invention the macromolecular film formingJ water soluble or water dispersable coating agent is a methacrylic resin.
In another preferred embodiment of the process according to the invention the macromolecular film forming, water soluble or water dispersable coating agent is gelatine.
In another preferred embodiment of the process according to the invention the coating fluid contains a-plasticizer.
In another preferred embodiment of the`process according to the invention the plasticizer is a glycerol.
In another preferred embodiment of the process according to the invention the glycerol is used in an amount of up to 60 % of the dry weight of the coating agent, preferably in an amount of between 10 and ~0 % of the dry weight of the coating agent.
In another preferred embodiment of the process according to the invention the concentration of the macromolecular film forming, water soluble or water dispersable coating agent in the coating fluid is between 2 and 50 weight-%.
In another preferre'd embodiment of the process according to the invention the concentration of the macromolecular film forming, water soluble or water dispersable coating agent in the coating fluid is between 4 and 10 weight-%.
In another preferred embodiment of the process according to the invention the mean diameter of the particles to be coated is between 0.1 and o.6 mm.
In another preferred embodiment of the process according to the invention the mean diameter of the particles to be coated is between 0.2 and o.6 mm.
1~4~334 1ll anot~le~ p~eferred em'~o~imerlt of tile p~ocess according to the invention the thlckness o~ the coating layer is be~ween 0.1 and 10 ~.
In another preferred embodiment o~ the process-according to the invention ~he thickness of the coating layer is between 0.5 and 1 ~. -The process according to the invention can be carried outin a continuous manner as well as batchwise. However, in a pre-ferred embodiment of the invention the process is carried out batchwise. In all the following examples the process is~ carried out batchwise.
The invention also encompasses a coated product comprising coated water soluble or water dispersable particles, whenever prepared by means of the process according to the invention.
The water soluble or water dispersable particles can be of any material which, for any reason, is to be coated. Examples of materials encompassed are enzyme additives, e.g. proteolytic enzyme additives for detergents, medicaments in pellet form, e.g.
oral penicillin preparations or hygroscopic substances, e.g.
fertilizers.
Coating of the particles is carried out for various reasons, e.g. in order to minimize dust formation, to protect against ultra-violet radiation, humidity or acidity, to minimize contamination, and the like.
The coating agent can be any macromolecular film forming, water soluble or water dispersable coating agent, e.g.
METHOCEL ~ MC 15: methyl cellulose of a methoxyl DS (Degree of Substitution) of 1.64 to 1.92 and o~ a DP (Degree of Poly-merization) corresponding to viscosities from 8 cP to 10,000 cP
in a 2 % aqueous solution at 20C.
TYLOSE ~ C 10: sodium carboxymethyl cellulose of a DS from 0.4 to 1.5 and a DP from 50 to 1000.
_ . ' , 10~9334 TYLoS~ 20: methylhydroxyeth~l cellulose (or hydroxyethylmethyl cellulose) of a methoxyl DS from 1.0 to
2.0, a hydroxyethyl DS from 0.1 to 0.5 and a DP from 50 to 1000.
l~ETHOCEL ~ XD 1181: hydroxypropylmethyl cellulose of a methoxyl DS from 1.0 to 2.0, a hydroxypropyl DS from 0.1 to 0.5, and a DP from 50 to 1000.
KOLLIDON ~ K 25 PVP: polyvinylpyrrolidone of an average molecular weight of 10,000, 40,000, 160,000 and 360,000 and mixtures thereof resulting in any intermediate average molecular weight.
CAR~30WAX ~ : polyethylene glycols of average mole-cular weights of 400, 600, 1000, 1540, 4000, 6000 and mixtures thereof of any intermediate average molecular weight.
EUDRAGIT ~ E 30 D: methacrylic resins, aqueous dispersions thereof. rrhis tablet lacquer is completely in-soluble in alkaline liquids.
SOLUGEL ~ : gelatine.
Polypropylene glycols.
Polyvinyl alcohols.
Alginates.
The concentration of the coating agent in the aqueous or substantially aqueous solution or dispersion corresponds to a viscosity which is suitable for atomization. Usually, as mentioned before, the concentration is between 2 and 50 weight-%, preferably between 4 and 10 weight-%. The limits, however, are highly dependent on the individual coating agent used. The average diameter of the particles to be coated is usually between 100 ~ and 600 to 1000 ~, preferably between 200 ~ and 600 ~. The relative humidity of the outlet air should usually not exceed 60%. The temperature of the air, which is used to fluidize the particles to be coated, should be adjusted in con-sideration of the nature of the particles to be coated.
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Th~ (lualit~ o'~ t~ oatir,cr, is not; in~luenced by the shape of the particles. F3y use of tile process of the invention it is possible to produce a perf~ct coating on splleres and on irregularly shaped particles as ~ell. Several of the known coating procedures are not well adapted to the coating of irregularly shaped particles which li are imperfectly coated, only. Therefore, the present process offers special advantages in connection with the coating of irregularly shaped particles. An example of such irregularly shaped particles is a prilled enzyme product includin~ prilled ALCALASE or ALCALASE P. When prilled ALCALASE is coated in accordance with the invention a product consisting of irregularly shaped particles having a-perfect coating is formed. Due to the irregular shape these particles have a very raduced tendency to segregate from the other particles of detergent compositions in powder form.
An additive consisting of spheroidal particles having a density different from the density of the particles of the other components of a powdery detergent composition will have a tendency to segregate from said other particles and thereby create an inhomogeneous detergent composition. The above irregularly shaped particles therefore offer special advantages.
According to the invention the coating fluid may contain a plasticizer such as triacetin, which is illustrated in the following example 2.
By using glycerol as a plasticizer in the coating fluid coated particles having specially advantageous dust levels can be obtained according to the invention.
By using glycerol as a plasticizer in the coating fluid in an amount of up to 60 per cent of the dry weight of the coating agent or up to the point when the coated particles are beginning to adhere to each other, preferably in an amount between 10 and ~0 per cent of the dry weight of the coating agent, the dust level of the coated particles is reduced significantly which will appear from the following.
~049334 rn o~de~ l;o ~i~e a bet~er ur)t1erstarl~ing of how to correla~e the different parameters of the process in order to obtain a relative humidity o~ the outlet air of less than 100~ the following calculation with reference to example 21 is presented. The inlet air, which was the air in the plant, had the following charac-teristics:
Temperature: 20C
Relative humidity: 50 ~ corresponding to 7 g of H20/kg air.
The rate of the coating fluidlwas 1700 ml/min. or 102 litre/hour. The coating fluid had a specific gravity of 1.0 g/cm~
and contained 10 % by weight of coating agent, corresponding to a water inlet amount from the coating fluid of 91.8 kg/hour.
The rate of fluidizing air was 8000 N m~/hour or 9600 kg of air/hour. Thus, the fluidizing air introduced 0.007 x 9600 =
67.2 kg of water in the systém per hour.
Thus, per hour a total of 91.8 + 67.2 kg of water was introduced into the system. This corresponds to~159.0 kg of water, which was removed from the system together with'about 9~00 kg of air. As the outlet air had a temperature of between 2~and 27C
this amount of humidity in the outlet air corresponds to a relative humidity in the outlet air of between 95 and 75 %. It is noted that this relative humidity is within the limit given for the relative humidity in claim 1.
In order to illustrate the invention the following examples are presented.
- Examples l to 10 illustrate the preparation of the coating fluid.
Example 1 Methyl cellulose (METHOCEL ~ MC 15) 50 g Deionized water 1000 g The methyl cellulose is triturated with about 33~ g of boiling water, after which the rest of the water (optionally cold) is added with s-ir~ing. The solutio~ is allowed to stand in a cold place.
- .
Exanple 2 Metilyl cellulose (ME~[~-IOCEL ~ MC 15) 50 g Deioni~ed water 1000 g Triacetin 5 g A solution of methyl cellulose and deionized water is pre-pared as described in Example 1, whereupon the triacetin is added.
Example 3 Sodium carboxymethyl cellulose (TYLOSE ~ C 10) 50 g Deionlzed water 1000 g The sodium carboxymethyl cellulose is dissolved in the water with stirringJ using a high speed mixer.
Example 4 Sodium carboxymethyl cellulose (TYLOSE ~ C 10) 100 g Deionized water 1000 g The sodium carboxymethyl cellulose is dissolved in the water with stirring~ using a high speed mixer.
Example 5 Methylhydroxyethyl cellulose ~YLOSE ~ MH 20) 50 g Deionized water lOpO g The methylhydroxyethyl cellulose is dissolved in the water with stirring, using a high speed mixér.
Example 6 Hydroxypropylmethyl cellulose (METHOCEL ~ XD 1181) 50 g Deionized water 1000 g The hydroxypropylmethyl cellulose is dissolved in the water with stirring, uslng a high speed mlxer.
Example 7 Gelatine (SOLUGEL ~ ) 50 g Deionized water 1000 g The gelatine is dissolved in the water with stirring, using a high speed mixer.
Example 8 Polyvinylpyrrolidone (KOLLIDON ~ K 25) 50 g Deionized water 1000 g The polyvinylpyrrolidone is dissolved in the water with stirring, using a high speed mixer.
Example 9 Polyethylene glycol (CARBOWAX ~ 4000) 50 g Deionized water 1000 g The polyethylene glycol is dissolved in the water with stirring, using a high speed mixer.
Example 10 Polyethylene glycol (CARBOWAX ~ 6000) 50 g Deionized water 1000 g The polyethylene glycol is dissolved in the water with stirring, using a high speed mixer.
The solutions prepared according to Examples 1 to 10 are used for the coating of prilled ALCALASE (ALCALASE P) in conventional and common fluid bed systems as stated in Examples 11 to 14 and 21.
Example 11 -Apparatus: "STREBA-l" (Aeromatic AG,Basel) ALCALASE P: 1000 g Nozzle ~.
- Pressure 2 1/2 ato .
Internal diameter 0.8 mm ~ .
Inlet temperature of -:
fluidizing air: 41-43C
: Temperature of parti-culate material: 31~-33C
; 30 Feed rate of coating fluid: 6 1/2 ml/min.
Fluidizing air: 8-10 scale units -.~. ' . ~ .
. ,; .i, ;
~ a !rl D ~
.__ Apparatus: "WS(i-5" (W. Glatt, Haltingen, Germany) ALCALASE P: 6000 g Mozzle Position of jacket: 0.5 Pressure 1 1/2 ato.
Internal diameter: 1.2 mm Inlet temperature of fluidizing air: -~2-45C
Temperature of O
particulate material: 31 -33 C
Feed rate of coating fluid: 35 ml/min.
Air velocity: 2 1/2 m/sec.
Example 13 . Apparatus: "WSG-30" (W. Glatt, Haltingen~
Germany) ALCALASE P:. ~5,000 g Nozzle - Position of jacket: 0.3 Pressure: 6 ato.
Internal diameter: 1.8 mm Inlet temperature of fluidizing air: ~2-45C .
Temperature of O 0 particulate material: 31 -33 C
Feed rate of coating fluid: 187 ml/min.
Fluidizing air: 5 scale units Example 14 Apparatus: "STREBA-60" (Aeromatic AG, Basel) ALCALASE P: 135 kg Nozzle Position of jacket: 1.0 Pressure: 6 ato.
Internal diameter: 2~ mm :i nlet te~ t,ure oP
fluidizing air: 42-l~5C
Temperat,ure of particulate material: 31-3~C
Feed rate of coating flu'id: 325 ml/min.
Rate Or fluidiæing air: corresponding to position 3 of damper.
In all cases particulate products are produced having remark-ably good properties.
The amount of coating layer on the ~articles and the amount of dust present in some of the coated products prepared according to Examples 12 to 14 appear from the following table II.
Table II
Coating fluid Amount of Amount of dust Example p~epared according coating layer on in ~g/100 g of prod~cr No. to Example No.coated product Total Enzyme 1 1 % 20 2.1 1 1 % 20 1.6 6 1 % , 5 o.8 12 1 1/2 ~ 20 2.6 % 1 5 1 . 8 1 1 1/2 % 20 0. 8 6 2 % 10 1.1
l~ETHOCEL ~ XD 1181: hydroxypropylmethyl cellulose of a methoxyl DS from 1.0 to 2.0, a hydroxypropyl DS from 0.1 to 0.5, and a DP from 50 to 1000.
KOLLIDON ~ K 25 PVP: polyvinylpyrrolidone of an average molecular weight of 10,000, 40,000, 160,000 and 360,000 and mixtures thereof resulting in any intermediate average molecular weight.
CAR~30WAX ~ : polyethylene glycols of average mole-cular weights of 400, 600, 1000, 1540, 4000, 6000 and mixtures thereof of any intermediate average molecular weight.
EUDRAGIT ~ E 30 D: methacrylic resins, aqueous dispersions thereof. rrhis tablet lacquer is completely in-soluble in alkaline liquids.
SOLUGEL ~ : gelatine.
Polypropylene glycols.
Polyvinyl alcohols.
Alginates.
The concentration of the coating agent in the aqueous or substantially aqueous solution or dispersion corresponds to a viscosity which is suitable for atomization. Usually, as mentioned before, the concentration is between 2 and 50 weight-%, preferably between 4 and 10 weight-%. The limits, however, are highly dependent on the individual coating agent used. The average diameter of the particles to be coated is usually between 100 ~ and 600 to 1000 ~, preferably between 200 ~ and 600 ~. The relative humidity of the outlet air should usually not exceed 60%. The temperature of the air, which is used to fluidize the particles to be coated, should be adjusted in con-sideration of the nature of the particles to be coated.
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~04~334 I
Th~ (lualit~ o'~ t~ oatir,cr, is not; in~luenced by the shape of the particles. F3y use of tile process of the invention it is possible to produce a perf~ct coating on splleres and on irregularly shaped particles as ~ell. Several of the known coating procedures are not well adapted to the coating of irregularly shaped particles which li are imperfectly coated, only. Therefore, the present process offers special advantages in connection with the coating of irregularly shaped particles. An example of such irregularly shaped particles is a prilled enzyme product includin~ prilled ALCALASE or ALCALASE P. When prilled ALCALASE is coated in accordance with the invention a product consisting of irregularly shaped particles having a-perfect coating is formed. Due to the irregular shape these particles have a very raduced tendency to segregate from the other particles of detergent compositions in powder form.
An additive consisting of spheroidal particles having a density different from the density of the particles of the other components of a powdery detergent composition will have a tendency to segregate from said other particles and thereby create an inhomogeneous detergent composition. The above irregularly shaped particles therefore offer special advantages.
According to the invention the coating fluid may contain a plasticizer such as triacetin, which is illustrated in the following example 2.
By using glycerol as a plasticizer in the coating fluid coated particles having specially advantageous dust levels can be obtained according to the invention.
By using glycerol as a plasticizer in the coating fluid in an amount of up to 60 per cent of the dry weight of the coating agent or up to the point when the coated particles are beginning to adhere to each other, preferably in an amount between 10 and ~0 per cent of the dry weight of the coating agent, the dust level of the coated particles is reduced significantly which will appear from the following.
~049334 rn o~de~ l;o ~i~e a bet~er ur)t1erstarl~ing of how to correla~e the different parameters of the process in order to obtain a relative humidity o~ the outlet air of less than 100~ the following calculation with reference to example 21 is presented. The inlet air, which was the air in the plant, had the following charac-teristics:
Temperature: 20C
Relative humidity: 50 ~ corresponding to 7 g of H20/kg air.
The rate of the coating fluidlwas 1700 ml/min. or 102 litre/hour. The coating fluid had a specific gravity of 1.0 g/cm~
and contained 10 % by weight of coating agent, corresponding to a water inlet amount from the coating fluid of 91.8 kg/hour.
The rate of fluidizing air was 8000 N m~/hour or 9600 kg of air/hour. Thus, the fluidizing air introduced 0.007 x 9600 =
67.2 kg of water in the systém per hour.
Thus, per hour a total of 91.8 + 67.2 kg of water was introduced into the system. This corresponds to~159.0 kg of water, which was removed from the system together with'about 9~00 kg of air. As the outlet air had a temperature of between 2~and 27C
this amount of humidity in the outlet air corresponds to a relative humidity in the outlet air of between 95 and 75 %. It is noted that this relative humidity is within the limit given for the relative humidity in claim 1.
In order to illustrate the invention the following examples are presented.
- Examples l to 10 illustrate the preparation of the coating fluid.
Example 1 Methyl cellulose (METHOCEL ~ MC 15) 50 g Deionized water 1000 g The methyl cellulose is triturated with about 33~ g of boiling water, after which the rest of the water (optionally cold) is added with s-ir~ing. The solutio~ is allowed to stand in a cold place.
- .
Exanple 2 Metilyl cellulose (ME~[~-IOCEL ~ MC 15) 50 g Deioni~ed water 1000 g Triacetin 5 g A solution of methyl cellulose and deionized water is pre-pared as described in Example 1, whereupon the triacetin is added.
Example 3 Sodium carboxymethyl cellulose (TYLOSE ~ C 10) 50 g Deionlzed water 1000 g The sodium carboxymethyl cellulose is dissolved in the water with stirringJ using a high speed mixer.
Example 4 Sodium carboxymethyl cellulose (TYLOSE ~ C 10) 100 g Deionized water 1000 g The sodium carboxymethyl cellulose is dissolved in the water with stirring~ using a high speed mixer.
Example 5 Methylhydroxyethyl cellulose ~YLOSE ~ MH 20) 50 g Deionized water lOpO g The methylhydroxyethyl cellulose is dissolved in the water with stirring, using a high speed mixér.
Example 6 Hydroxypropylmethyl cellulose (METHOCEL ~ XD 1181) 50 g Deionized water 1000 g The hydroxypropylmethyl cellulose is dissolved in the water with stirring, uslng a high speed mlxer.
Example 7 Gelatine (SOLUGEL ~ ) 50 g Deionized water 1000 g The gelatine is dissolved in the water with stirring, using a high speed mixer.
Example 8 Polyvinylpyrrolidone (KOLLIDON ~ K 25) 50 g Deionized water 1000 g The polyvinylpyrrolidone is dissolved in the water with stirring, using a high speed mixer.
Example 9 Polyethylene glycol (CARBOWAX ~ 4000) 50 g Deionized water 1000 g The polyethylene glycol is dissolved in the water with stirring, using a high speed mixer.
Example 10 Polyethylene glycol (CARBOWAX ~ 6000) 50 g Deionized water 1000 g The polyethylene glycol is dissolved in the water with stirring, using a high speed mixer.
The solutions prepared according to Examples 1 to 10 are used for the coating of prilled ALCALASE (ALCALASE P) in conventional and common fluid bed systems as stated in Examples 11 to 14 and 21.
Example 11 -Apparatus: "STREBA-l" (Aeromatic AG,Basel) ALCALASE P: 1000 g Nozzle ~.
- Pressure 2 1/2 ato .
Internal diameter 0.8 mm ~ .
Inlet temperature of -:
fluidizing air: 41-43C
: Temperature of parti-culate material: 31~-33C
; 30 Feed rate of coating fluid: 6 1/2 ml/min.
Fluidizing air: 8-10 scale units -.~. ' . ~ .
. ,; .i, ;
~ a !rl D ~
.__ Apparatus: "WS(i-5" (W. Glatt, Haltingen, Germany) ALCALASE P: 6000 g Mozzle Position of jacket: 0.5 Pressure 1 1/2 ato.
Internal diameter: 1.2 mm Inlet temperature of fluidizing air: -~2-45C
Temperature of O
particulate material: 31 -33 C
Feed rate of coating fluid: 35 ml/min.
Air velocity: 2 1/2 m/sec.
Example 13 . Apparatus: "WSG-30" (W. Glatt, Haltingen~
Germany) ALCALASE P:. ~5,000 g Nozzle - Position of jacket: 0.3 Pressure: 6 ato.
Internal diameter: 1.8 mm Inlet temperature of fluidizing air: ~2-45C .
Temperature of O 0 particulate material: 31 -33 C
Feed rate of coating fluid: 187 ml/min.
Fluidizing air: 5 scale units Example 14 Apparatus: "STREBA-60" (Aeromatic AG, Basel) ALCALASE P: 135 kg Nozzle Position of jacket: 1.0 Pressure: 6 ato.
Internal diameter: 2~ mm :i nlet te~ t,ure oP
fluidizing air: 42-l~5C
Temperat,ure of particulate material: 31-3~C
Feed rate of coating flu'id: 325 ml/min.
Rate Or fluidiæing air: corresponding to position 3 of damper.
In all cases particulate products are produced having remark-ably good properties.
The amount of coating layer on the ~articles and the amount of dust present in some of the coated products prepared according to Examples 12 to 14 appear from the following table II.
Table II
Coating fluid Amount of Amount of dust Example p~epared according coating layer on in ~g/100 g of prod~cr No. to Example No.coated product Total Enzyme 1 1 % 20 2.1 1 1 % 20 1.6 6 1 % , 5 o.8 12 1 1/2 ~ 20 2.6 % 1 5 1 . 8 1 1 1/2 % 20 0. 8 6 2 % 10 1.1
3 % lo o.8 . -. .. _.
1 % 5 ~ 1.8 1 1/2 % 20 1.0 3 1 1 % 5 l.o 1 % lo 1.6 14 1 1/2 % 5o ~.4 1 1 % 15 1.6 Examples 15 to 20 illustrate the preparation of a coating fluid containing glycerol and corresponding coating fluids without glycerol.
.
' ' ' .
`'~' ' 1~49334 ~`xa.~t~
Methyl cell~llose (M~ HOCEL ~ MC 15) 50 g Deioni,zed water 950 g The methyl cellulose is triturated with about 33~ g Or boiling water, after which the rest Or the water (optionally cold) is added with stirring. The solution is allowed to stand in a cold place.
Example 16 Methyl cellulose (METHOCEL ~ MC 15) 42.5 g Glycerol 7,5 g Deionized water 950.0 g A solution of methyl cellulose and deionized water is prepared as described in Example 15, whereupon the glycerol is added.
Example 17 Sodium carboxymethyl cellulose (CELLOFAS ~ B 5) 100 g Deionized water 900 g The sodium carboxymethyl cellulose is triturated with about 3~3 g of boiling water, after which the rest of the water (optionally cold) is added with stirring. The solution is allowed to stand in a cold place.
Example 18 Sodium carboxymethyl cellulose (CELLOFAS ~ B 5) 85 g Glycerol ~ 15-g Deionized water 900 g A solution of sodium carboxymethyl cellulose and deionized water is prepared as described in Example 17, whereupon the glycerol is added.
Example 19 Sodium carboxymethyl cellulose (CEKOL ~ HS) 10,0 g Deionized water 900 g A solution af sodium carboxymethyl cellulose and deionized water is prepared as described in Example 17.
, -14-. .
.
.. .... . . .
~049334 E~ample 20 Sodium carbox~methyl cellulose (CEKOL ~ HS) 85 g Glycerol 15 g Deionized water goo g A solution of sodium carboxymethyl cellulose and deionized water is prepared as described in Example 17, whereupon the glycerol is added.
The solutions prepared according to Examples 15 to 20 are used for the co~ting o~ ALCALASE M in a fluid bed system as stated in Example 21 Example 21 Apparatus: "WSG-300" (W. Glatt, Haltingen, Gerrr~any) ALCALASE M: 600 kg Nozzle six-headed nozzle Internal diameter: 1.2 mm -~
Jacket diameter: 6.o mm Pressure: 6.o ato.
Inlet temperature of fluidizing air: 46-50C
Temperature of particulate material: 23-27C
Feed rate of coating fluid: 1700 ml/min.
Fluidizing air: 8000 N m3/hour In all cases particulate products are produced having rernark-ably good properties, especially in regard to the dust level.
The amount Or dust present in the coated products prepared according to Example 21 appears from the following table III.
. ' '. ' 109~334 'ilat~Le-:r~:r Coating ~ id Amount of Amount of dust Example prepared accordil~K coating layer on in ug/100 g of~Eroduct No. to E~'xarnple No. coated product Total Enzvme . _ _ _ _ _Y
. 1 % 20 1.2 16 1 % 10 0.5 21 17 1 ~ 15 1.6 1~ 1 % 10 0.7 19 1 ~ 30 1.~
1 ~ 10 0.8 . . _ It appears from the above table III ~hat by using glycerol as a plasticizer in the coating fluid a remarka'~ly advantageous effect on the dust level of the coated particles is obtained.
.
.
1 % 5 ~ 1.8 1 1/2 % 20 1.0 3 1 1 % 5 l.o 1 % lo 1.6 14 1 1/2 % 5o ~.4 1 1 % 15 1.6 Examples 15 to 20 illustrate the preparation of a coating fluid containing glycerol and corresponding coating fluids without glycerol.
.
' ' ' .
`'~' ' 1~49334 ~`xa.~t~
Methyl cell~llose (M~ HOCEL ~ MC 15) 50 g Deioni,zed water 950 g The methyl cellulose is triturated with about 33~ g Or boiling water, after which the rest Or the water (optionally cold) is added with stirring. The solution is allowed to stand in a cold place.
Example 16 Methyl cellulose (METHOCEL ~ MC 15) 42.5 g Glycerol 7,5 g Deionized water 950.0 g A solution of methyl cellulose and deionized water is prepared as described in Example 15, whereupon the glycerol is added.
Example 17 Sodium carboxymethyl cellulose (CELLOFAS ~ B 5) 100 g Deionized water 900 g The sodium carboxymethyl cellulose is triturated with about 3~3 g of boiling water, after which the rest of the water (optionally cold) is added with stirring. The solution is allowed to stand in a cold place.
Example 18 Sodium carboxymethyl cellulose (CELLOFAS ~ B 5) 85 g Glycerol ~ 15-g Deionized water 900 g A solution of sodium carboxymethyl cellulose and deionized water is prepared as described in Example 17, whereupon the glycerol is added.
Example 19 Sodium carboxymethyl cellulose (CEKOL ~ HS) 10,0 g Deionized water 900 g A solution af sodium carboxymethyl cellulose and deionized water is prepared as described in Example 17.
, -14-. .
.
.. .... . . .
~049334 E~ample 20 Sodium carbox~methyl cellulose (CEKOL ~ HS) 85 g Glycerol 15 g Deionized water goo g A solution of sodium carboxymethyl cellulose and deionized water is prepared as described in Example 17, whereupon the glycerol is added.
The solutions prepared according to Examples 15 to 20 are used for the co~ting o~ ALCALASE M in a fluid bed system as stated in Example 21 Example 21 Apparatus: "WSG-300" (W. Glatt, Haltingen, Gerrr~any) ALCALASE M: 600 kg Nozzle six-headed nozzle Internal diameter: 1.2 mm -~
Jacket diameter: 6.o mm Pressure: 6.o ato.
Inlet temperature of fluidizing air: 46-50C
Temperature of particulate material: 23-27C
Feed rate of coating fluid: 1700 ml/min.
Fluidizing air: 8000 N m3/hour In all cases particulate products are produced having rernark-ably good properties, especially in regard to the dust level.
The amount Or dust present in the coated products prepared according to Example 21 appears from the following table III.
. ' '. ' 109~334 'ilat~Le-:r~:r Coating ~ id Amount of Amount of dust Example prepared accordil~K coating layer on in ug/100 g of~Eroduct No. to E~'xarnple No. coated product Total Enzvme . _ _ _ _ _Y
. 1 % 20 1.2 16 1 % 10 0.5 21 17 1 ~ 15 1.6 1~ 1 % 10 0.7 19 1 ~ 30 1.~
1 ~ 10 0.8 . . _ It appears from the above table III ~hat by using glycerol as a plasticizer in the coating fluid a remarka'~ly advantageous effect on the dust level of the coated particles is obtained.
.
.
Claims (23)
1. A process for coating water soluble or water dispersible particles by means of the fluid bed technique, which comprises introducing the particles to be coated in a fluid bed reactor, the mean diameter of the particles to be coated being in the range of from 0.1 to 0.6 mm, and introducing a coating fluid essentially consisting of an aqueous or substantially aqueous solution or dispersion of a macromolecular film forming, water soluble or water dispersible coating agent by means of atomi-zation, wherein the relative humidity of the outlet air from the fluid bed reactor is below 100% and wherein the maximum size of the atomized droplets of the coating fluid does not exceed the minimum size of the particles to be coated.
2. A process as claimed in claim 1, wherein the water soluble or water dispersible particles to be coated contain as an active ingredient one or more enzymes.
3. A process as claimed in claim 2, wherein the enzyme is bacterial proteinase.
4. A process as claimed in claim 3, wherein the bacterial proteinase is precoated in order to reduce dust formation.
5. A process as claimed in claim 4, wherein the bacterial proteinase is microbial proteinase.
6. A process as claimed in claim 3, wherein the bacterial proteinase is alkaline resistant proteinase.
7. A process as claimed in claim 2, wherein the enzyme or is bacterial or fungal carbohydrase.
8. A process as claimed in claim 7, wherein the bacterial amylase is thermally stable amylases.
9. A process as claimed in claim 1, wherein the macromolecular film forming, water soluble or water dispersible coating agent is a cellulose derivative.
10. A process as claimed in claim 9, wherein the cellulose derivative is methyl cellulose, hydroxybutylmethyl cellulose, sodium carboxymethyl cellulose, hydroxyethylmethyl cellulose or hydroxypropylmethyl cellulose.
11. A process as claimed in claims 1, 2 or 3, wherein the macromolecular film forming, water soluble or water dispersible coating agent is a polyvinylpyrrolidone.
12. A process as claimed in claims 1, 2 or 3, wherein the macromolecular film forming, water soluble or water dispersible coating agent is a polyethylene glycol, preferably of a molecular weight of between about 400 and about 6000.
13. A process as claimed in claims 1, 2 or 3, wherein the macromolecular film forming, water soluble or water dispersible coating agent is a methacrylic resin.
14. A process as claimed in claims 1, 2 or 3, wherein the macromolecular film forming, water soluble or water dispersible coating agent is a gelatine.
15. A process as claimed in claim 1, wherein the coating fluid contains a plasticizer.
16. A process as claimed in claim 15, wherein the plastici-zer is glycerol.
17. A process as claimed in claim 16, wherein the glycerol is used in an amount of up to 60% of the dry weight of the coat-ing agent, preferably in an amount between 10 and 30% of the dry weight of the coating agent.
18. A process as claimed in claim 9, wherein the concentration of the macromolecular film forming, water soluble or water dispersible coating agent in the coating fluid is between 2 and 50 weight-%.
19. A process as claimed in claim 18, wherein the concentration of the macromolecular film forming, water soluble or water dispersible coating agent in the coating fluid is between 4 and 10 weight-%.
20. A process as claimed in claim 1, in which the mean diameter of the particles to be coated is between 0.2 and 0.6 mm.
21. A process as claimed in claim 1, in which the thick-ness of the coating layer is between 0.1 and 10 µ.
22. A process as claimed in claim 21, in which the thick-ness of the coating layer is between 0.5 and 1 µ.
23. A process as claimed in claims 1, 2 or 3, in which the coating operation is performed batchwise.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB34993/73A GB1483591A (en) | 1973-07-23 | 1973-07-23 | Process for coating water soluble or water dispersible particles by means of the fluid bed technique |
GB1084274 | 1974-03-11 |
Publications (1)
Publication Number | Publication Date |
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CA1049334A true CA1049334A (en) | 1979-02-27 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CA205,367A Expired CA1049334A (en) | 1973-07-23 | 1974-07-22 | Process for coating water soluble or water dispersible particles by means of the fluid bed technique |
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JP (1) | JPS5071583A (en) |
AT (1) | AT357979B (en) |
AU (1) | AU498649B2 (en) |
BE (1) | BE817930A (en) |
CA (1) | CA1049334A (en) |
CH (1) | CH604923A5 (en) |
DE (1) | DE2435008A1 (en) |
DK (1) | DK384574A (en) |
ES (1) | ES428475A1 (en) |
FI (1) | FI219474A (en) |
FR (1) | FR2238530B1 (en) |
GB (1) | GB1483591A (en) |
IE (1) | IE41403B1 (en) |
IT (1) | IT1016947B (en) |
NL (1) | NL7409683A (en) |
SE (1) | SE7409471L (en) |
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-
1973
- 1973-07-23 GB GB34993/73A patent/GB1483591A/en not_active Expired
-
1974
- 1974-07-12 CH CH965874A patent/CH604923A5/xx not_active IP Right Cessation
- 1974-07-17 DK DK384574A patent/DK384574A/da not_active Application Discontinuation
- 1974-07-17 NL NL7409683A patent/NL7409683A/en not_active Application Discontinuation
- 1974-07-18 FI FI2194/74A patent/FI219474A/fi unknown
- 1974-07-19 SE SE7409471A patent/SE7409471L/xx unknown
- 1974-07-20 DE DE2435008A patent/DE2435008A1/en not_active Ceased
- 1974-07-22 CA CA205,367A patent/CA1049334A/en not_active Expired
- 1974-07-22 IT IT52219/74A patent/IT1016947B/en active
- 1974-07-22 BE BE146802A patent/BE817930A/en not_active IP Right Cessation
- 1974-07-22 ES ES428475A patent/ES428475A1/en not_active Expired
- 1974-07-23 AT AT606874A patent/AT357979B/en active
- 1974-07-23 AU AU71557/74A patent/AU498649B2/en not_active Expired
- 1974-07-23 JP JP49084519A patent/JPS5071583A/ja active Pending
- 1974-07-23 FR FR7425523A patent/FR2238530B1/fr not_active Expired
- 1974-07-23 IE IE1568/74A patent/IE41403B1/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4828882A (en) * | 1987-03-16 | 1989-05-09 | Canadian Patents & Developments Limited | Particle encapsulation technique |
US5211985A (en) * | 1991-10-09 | 1993-05-18 | Ici Canada, Inc. | Multi-stage process for continuous coating of fertilizer particles |
US5399186A (en) * | 1991-10-09 | 1995-03-21 | Ici Canada, Inc. | Apparatus and process for coating particles |
Also Published As
Publication number | Publication date |
---|---|
DE2435008A1 (en) | 1975-02-06 |
IE41403L (en) | 1975-01-23 |
FR2238530A1 (en) | 1975-02-21 |
IT1016947B (en) | 1977-06-20 |
DK384574A (en) | 1975-03-03 |
AU498649B2 (en) | 1979-03-22 |
BE817930A (en) | 1975-01-22 |
SE7409471L (en) | 1975-01-24 |
GB1483591A (en) | 1977-08-24 |
FI219474A (en) | 1975-01-24 |
CH604923A5 (en) | 1978-09-15 |
JPS5071583A (en) | 1975-06-13 |
ATA606874A (en) | 1980-01-15 |
ES428475A1 (en) | 1976-12-16 |
IE41403B1 (en) | 1980-01-02 |
FR2238530B1 (en) | 1979-03-09 |
AU7155774A (en) | 1976-01-29 |
NL7409683A (en) | 1975-01-27 |
AT357979B (en) | 1980-08-11 |
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