US3406119A - Encapsulation - Google Patents

Encapsulation Download PDF

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Publication number: US3406119A
Authority: US; United States
Prior art keywords: capsules; oil; albumin; particles; water
Prior art date: 1965-03-05
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.): Expired - Lifetime

Application number

US437464A

Inventor

Kosar Jaromir

Jr George M Atkins

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Keuffel and Esser Co

Original Assignee

Keuffel and Esser Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1965-03-05

Filing date

1965-03-05

Publication date

1968-10-15

1965-03-05 Application filed by Keuffel and Esser Co filed Critical Keuffel and Esser Co

1965-03-05 Priority to US437464A priority Critical patent/US3406119A/en

1966-03-03 Priority to DE19661542261 priority patent/DE1542261A1/en

1966-03-04 Priority to FR52142A priority patent/FR1470723A/en

1966-03-04 Priority to GB9698/66A priority patent/GB1126856A/en

1968-10-15 Application granted granted Critical

1968-10-15 Publication of US3406119A publication Critical patent/US3406119A/en

1982-03-25 Assigned to CONTINENTAL ILLINOIS NATIONAL BANK & TRUST CO., OF CHICAGO, A NATIONAL BANKING ASSOCIATION, CHASE MANHATTAN BANK, N.A. THE; A NATIONAL BANKING ASSOCIATION, BANK OF CALIFORNIA N.A. THE; A NATIONAL BANKING ASSOCIATION, SECURITY NATIONAL BANK, A NATIONAL BANKING ASSOCIATION FOR ITSELF AND AS AGENT FOR CITIBANK, N.A. A NATIONAL BANKING ASSOCIATION, CHEMICAL BANK, A BANKING INSTITUTION OF reassignment CONTINENTAL ILLINOIS NATIONAL BANK & TRUST CO., OF CHICAGO, A NATIONAL BANKING ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KEUFFEL & ESSER COMPANY A.N.J. CORP

1985-10-15 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- 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
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/28—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating
- B41M5/287—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating using microcapsules or microspheres only
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]

Definitions

One prior art material provides for two layers of reactants separated by a third fusible intermediate layer. Heating the composite layers causes melting of the fusible intermediate layer, thereby allowing the two outer layers to commingle and react. The reactants are thus separated by the intermediate layer until needed. This provides convenience for the user since one of the reactants need not be held in reserve and added at the desired time.
Another method of isolating at least one of the reactants is to encapsulate the item in a shell or envelope of unreactive material. When needed, the reactant is made available by breaking the shell.
One form of capsule is the developer pod used in the photographic art. These pods or capsules contain the active ingredients necessary to rapidly develop exposed photographic images. The capsules are broken physically by squeezing.
capsules presents a handicap for some applications, and therefore, capsules of fine size have been developed. These find use in such specific and varied applications as food flavorings, medicines, and photography. Some of the advantages afforded by the use of such capsules in the photographic art are isolation of reactants until desired, coating simplicity, convenience in development, indefinitely long storage life for sensitized materials, (and fine resolutions).
the present invention provides a novel method for making simple capsules.
This method involves the discovery that certain materials can be dissolved in water at room temperature and be precipitated from the water at elevated temperatures.
polymer A is dissolved in water at one temperature.
Water-immiscible material B is then added to the solution and dispersed to a fine size.
the dispersion is then heated until the polymer coagulates around the particles or globules.
the resuplting capsules may then be filtered, hardened, and dried.
one object of the present invention is to provide capsules and novel methods for making capsules.
Another object is to provide methods for encapsulating material by means of heat, and providing capsules so formed.
the objects of the present invention may be realized by dissolving a heat-coagulatable polymer or colloid in cold water, dispersing a water-immiscible oil or solid in the solution, and then heating the dispersion to coagulate the polymer around the particles in the form of a shell.
FIGURE 1 is a flow sheet of the present method.
FIGURE 2 is a capsule of the present invention.
step 1A a water-immiscible material is dispersed in an aqueous solution of heat-coagulateable polymer to form a dispersion of particles.
step 1B the dispersion is heated to coagulate polymer on the particles as shells, thereby producing discrete capsules.
Optional steps not shown in FIGURE 1 include separation of the capsules from the solution, washing the capsules, and drying the capsules.
the capsule 20 of FIGURE 2 comprises core 21 and shell 22.
Core 21 comprises water-immiscible material which may be solid or liquid.
Shell 22 comprises heatcoagulated polymer completely surrounding core 21 and substantially impervious to the core material 21.
Egg albumin coagulates at temperatures of 60-70 C., but it was found that lower temperatures are suitable for the present invention. Blood albumin was also suitable.
Albumin capsules do not form the hard agglomerates that casein capsules do and therefore offer greater advantages in coating applications where uniformity is desirable. As with casein capsules, however, use of an antifoaming agent is helpful. Silicones have served effectively as an anti-foam agents for albumin sols.
Ratios of 7.5 parts oil to one part albumin have been successfully used.
the range may vary from 1:1 to 10:1.
coagulation by means of heat can be effected in any of several ways.
the size of the capsule is determined by the size of the oil droplet in the oil-in-water emulsion. Particle sizes preferably range [from 1 micron to 50 microns in diameter. The particles may be solid or liquid at the time of shell-formation.
Example 1 10 grams of egg albumin were dissolved in 200 ml. of water at room temperature. Seven drops of a 30% silicone anti-foam (Antifoam 60) were added to the albumin s01. Added next was 20 ml. of cotton seed oil in which was dissolved 0.5 gram of an oil black dye (CI Solvent Black 12). An emulsion was made using an air-powered mechanical stirrer. An electrical hot plate was used to heat the emulsion to 70 C. and thereby form capsules. Stirring was continued throughout the heating process. The capsules were then filtered from the solution.
Antifoam 60 a 30% silicone anti-foam
CI Solvent Black 12 an oil black dye
the capsules were spherical and ranged from 5 to 50 microns in diameter. They were placed in acetone to test the imperviousness of the capsule shell. No color was imparted to the acetone phase. The capsules were then crushed to release the dyed oil. The acetone then took on the color of the dye.
oil soluble dye is not necessary for the encapsulation of material. It was used here to show that the oil could be a carrier for another material and as a marking material to demonstrate the imperviousness of the capsule shell.
Example 2 grams of egg albumin were dissolved in cold water and 7 drops of a silicone anti-foam agent were added. 0.5 gram of carbon tetrabromide and 0.2 gram of Cyasorb IR-117 infrared radiation absorber were dissolved in 20 ml. of cotton seed oil and added to the albumin sol. An air powered stirrer was used to emulsify the oil in the aqueous phase. With continued stirring, the emulsion was exposed to an infrared lamp (reflecting drying lamp, 250 watt) in order to cause coagulation of the egg albumin as shells around the oil droplets. Samples to be inspected under the microscope were obtained with a pipette.
infrared lamp reflecting drying lamp, 250 watt
Capsules were already present when the temperature of the aqueous phase reached C. When the temperature of the aqueous phase reached C., the mixture was filtered. The capsules thus obtained were washed with acetone and the filtrate mixed with diphenylamine and exposed to a UV light source (500 watt projection lamp). No color developed. The capsules were then crushed in acetone, the filtrate mixed with diphenylamine, and the mixture exposed to the light source. A blue color was formed. Carbon black was also suitable and an infrared absorber.
Example 3 10 grams of egg albumin were dissolved in 200 ml. of water. Five drops of a 30% silicone anti-foaming agent were added to the albumin sol. Two grams of carbon tetrabromide were dissolved in 20 ml. of Castor oil and placed, along with the albumin sol, into a Waring Blendor (model CB4). An oil in water emulsion was prepared by operating the blender at 17,000 rpm. After two minutes of operation, 500 ml. of boiling water were added to form the capsules and the stirring was continued for another 1 /2 minutes. The capsules were then filtered from the solution.
a Waring Blendor model CB4
the capsules were spherical and about 10 microns in diameter. They were washed with benzene and the filtrate was mixed with diphenylamine and exposed to a strong light source. No color was formed. The capsules were then crushed in the benzene and the filtrate was mixed with diphenylamine and exposed to light source. A deep blue color developed as in Example 2.
a method of making capsules comprising:
a method of making capsules comprising:
a method of making capsules comprising:

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Dispersion Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Manufacturing Of Micro-Capsules (AREA)

Description

Oct. 15, 1968 J. KOSAR ET AL 3,406,119

ENCAPSULATION Filed March 5, 1965 FIG.I

A DISPENSING WATER- IMMISCIBLE MATERIAL IN AQUEOUS SOLUTION OF HEAT- COAGULATABLE POLYMER TO FORM A DISPERSION OF PARTICLES B HEATING THE DISPERSION TO COAGULATE POLYMER ON THE PARTICLES AS SHELLS FIGQ CAPSULE 2O CORE 2I SHELL 22 lNVE/VTORS JAROMIR KOSAR GEORGE M. ATKINS JR.

ATTORNEY United States Patent 3,406,119 EN CAPSULATION Jaromir Kosar, Beechhurst, N.Y., and George M. Atkins, Jr., Atlanta, Ga., assignors to Keufiel & Esser Company, Hoboken, N J a corporation of New Jersey Filed Mar. 5, 1965, Ser. No. 437,464 3 Claims. (Cl. 252-316) ABSTRACT OF THE DISCLOSURE The method of forming capsules by the heat coagula tion of an albuminabout particles or droplets of water- The present invention relates to encapsulation and refers more particularly to capsules and methods for making capsules.

In many instances it is convenient to have two or more reactive agents in close proximity to each other in order to react promptly and uniformly. One prior art material provides for two layers of reactants separated by a third fusible intermediate layer. Heating the composite layers causes melting of the fusible intermediate layer, thereby allowing the two outer layers to commingle and react. The reactants are thus separated by the intermediate layer until needed. This provides convenience for the user since one of the reactants need not be held in reserve and added at the desired time.

Another method of isolating at least one of the reactants is to encapsulate the item in a shell or envelope of unreactive material. When needed, the reactant is made available by breaking the shell. One form of capsule is the developer pod used in the photographic art. These pods or capsules contain the active ingredients necessary to rapidly develop exposed photographic images. The capsules are broken physically by squeezing.

The size of the capsules presents a handicap for some applications, and therefore, capsules of fine size have been developed. These find use in such specific and varied applications as food flavorings, medicines, and photography. Some of the advantages afforded by the use of such capsules in the photographic art are isolation of reactants until desired, coating simplicity, convenience in development, indefinitely long storage life for sensitized materials, (and fine resolutions).

Previous methods for making miorocapsules have used high molecular weight polymers and natural colloids for shell materials. When two colloids having different isoelectric points are used, proper adjustment of the pH produces compound capsules.

The present invention provides a novel method for making simple capsules. This method involves the discovery that certain materials can be dissolved in water at room temperature and be precipitated from the water at elevated temperatures. Thus, for example, polymer A is dissolved in water at one temperature. Water-immiscible material B is then added to the solution and dispersed to a fine size. The dispersion is then heated until the polymer coagulates around the particles or globules. The resuplting capsules may then be filtered, hardened, and dried.

ice

Therefore, one object of the present invention is to provide capsules and novel methods for making capsules.

Another object is to provide methods for encapsulating material by means of heat, and providing capsules so formed.

Other objects of the present invention will become apparent in the course of the following specification.

The objects of the present invention may be realized by dissolving a heat-coagulatable polymer or colloid in cold water, dispersing a water-immiscible oil or solid in the solution, and then heating the dispersion to coagulate the polymer around the particles in the form of a shell.

In the drawing:

FIGURE 1 is a flow sheet of the present method; and

FIGURE 2 is a capsule of the present invention.

The process of FIGURE 1 shows two steps. In step 1A, a water-immiscible material is dispersed in an aqueous solution of heat-coagulateable polymer to form a dispersion of particles. In step 1B, the dispersion is heated to coagulate polymer on the particles as shells, thereby producing discrete capsules. Optional steps not shown in FIGURE 1 include separation of the capsules from the solution, washing the capsules, and drying the capsules.

The capsule 20 of FIGURE 2 comprises core 21 and shell 22. Core 21 comprises water-immiscible material which may be solid or liquid. Shell 22 comprises heatcoagulated polymer completely surrounding core 21 and substantially impervious to the core material 21.

Egg albumin coagulates at temperatures of 60-70 C., but it was found that lower temperatures are suitable for the present invention. Blood albumin was also suitable.

Albumin capsules do not form the hard agglomerates that casein capsules do and therefore offer greater advantages in coating applications where uniformity is desirable. As with casein capsules, however, use of an antifoaming agent is helpful. Silicones have served effectively as an anti-foam agents for albumin sols.

Ratios of 7.5 parts oil to one part albumin have been successfully used. The range may vary from 1:1 to 10:1. As can be seen in the examples, coagulation by means of heat can be effected in any of several ways. The size of the capsule is determined by the size of the oil droplet in the oil-in-water emulsion. Particle sizes preferably range [from 1 micron to 50 microns in diameter. The particles may be solid or liquid at the time of shell-formation.

The following examples further illustrate the present invention and are not intended to limit the scope of the inventive concept.

Example 1 10 grams of egg albumin were dissolved in 200 ml. of water at room temperature. Seven drops of a 30% silicone anti-foam (Antifoam 60) were added to the albumin s01. Added next was 20 ml. of cotton seed oil in which was dissolved 0.5 gram of an oil black dye (CI Solvent Black 12). An emulsion was made using an air-powered mechanical stirrer. An electrical hot plate was used to heat the emulsion to 70 C. and thereby form capsules. Stirring was continued throughout the heating process. The capsules were then filtered from the solution.

The capsules were spherical and ranged from 5 to 50 microns in diameter. They were placed in acetone to test the imperviousness of the capsule shell. No color was imparted to the acetone phase. The capsules were then crushed to release the dyed oil. The acetone then took on the color of the dye.

It should be evident that the presence of the oil soluble dye is not necessary for the encapsulation of material. It was used here to show that the oil could be a carrier for another material and as a marking material to demonstrate the imperviousness of the capsule shell.

Example 2 grams of egg albumin were dissolved in cold water and 7 drops of a silicone anti-foam agent were added. 0.5 gram of carbon tetrabromide and 0.2 gram of Cyasorb IR-117 infrared radiation absorber were dissolved in 20 ml. of cotton seed oil and added to the albumin sol. An air powered stirrer was used to emulsify the oil in the aqueous phase. With continued stirring, the emulsion was exposed to an infrared lamp (reflecting drying lamp, 250 watt) in order to cause coagulation of the egg albumin as shells around the oil droplets. Samples to be inspected under the microscope were obtained with a pipette. Capsules were already present when the temperature of the aqueous phase reached C. When the temperature of the aqueous phase reached C., the mixture was filtered. The capsules thus obtained were washed with acetone and the filtrate mixed with diphenylamine and exposed to a UV light source (500 watt projection lamp). No color developed. The capsules were then crushed in acetone, the filtrate mixed with diphenylamine, and the mixture exposed to the light source. A blue color was formed. Carbon black was also suitable and an infrared absorber.

Example 3 10 grams of egg albumin were dissolved in 200 ml. of water. Five drops of a 30% silicone anti-foaming agent were added to the albumin sol. Two grams of carbon tetrabromide were dissolved in 20 ml. of Castor oil and placed, along with the albumin sol, into a Waring Blendor (model CB4). An oil in water emulsion was prepared by operating the blender at 17,000 rpm. After two minutes of operation, 500 ml. of boiling water were added to form the capsules and the stirring was continued for another 1 /2 minutes. The capsules were then filtered from the solution.

The capsules were spherical and about 10 microns in diameter. They were washed with benzene and the filtrate was mixed with diphenylamine and exposed to a strong light source. No color was formed. The capsules were then crushed in the benzene and the filtrate was mixed with diphenylamine and exposed to light source. A deep blue color developed as in Example 2.

It is apparent that the described examples are capable of many variations and modifications. All such variations and modifications are to be included within the scope of the present invention.

What is claimed is:

1. A method of making capsules comprising:

dispersing between about one and ten parts of a waterimmiscible oil containing a carbon black infrared absorber into an aqueous solution comprising about one part of a heat-coagulatable albumin to form a dispersion of oil particles; and

exposing said dispersion to infrared radiation for a time suflicient to coagulate said albumin at the surface of said particles.

2. A method of making capsules comprising:

dispersing between about one and ten parts of a waterimmiscible oil containing a carbon black infrared absorber into an aqueous solution comprising about one part of egg albumin to form a dispersion of oil particles in the aqueous vehicle; and

exposing said dispersion to infrared radiation for a time suflicient to heat said particles to the coagulation temperature of said albumin, whereby said albumin coagulates on the surface of said particles.

3. A method of making capsules comprising:

dispersing between about one and ten parts of a Waterimmiscible, carbon black-containing oil in an aqueous solution comprising about one part of egg albumin to form a dispersion of oil particles in the aqueous vehicle; and

exposing said dispersion to infrared radiation for a time sufficient to heat the albumin at the surface of said particles to a temperature of about -70 C., thereby coagulating said albumin to form capsule walls about said particles.

References Cited UNITED STATES PATENTS 6/1964 Soloway 252316 X 6/1965 Brynko et al. 252-316

US437464A 1965-03-05 1965-03-05 Encapsulation Expired - Lifetime US3406119A (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
US437464A US3406119A (en)	1965-03-05	1965-03-05	Encapsulation
DE19661542261 DE1542261A1 (en)	1965-03-05	1966-03-03	Process for the production of capsules containing liquids or solids
FR52142A FR1470723A (en)	1965-03-05	1966-03-04	Process for preparing capsules containing liquids or solids
GB9698/66A GB1126856A (en)	1965-03-05	1966-03-04	Improvements in and relating to encapsulation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US437464A US3406119A (en)	1965-03-05	1965-03-05	Encapsulation

Publications (1)

Publication Number	Publication Date
US3406119A true US3406119A (en)	1968-10-15

Family

ID=23736565

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US437464A Expired - Lifetime US3406119A (en)	1965-03-05	1965-03-05	Encapsulation

Country Status (4)

Country	Link
US (1)	US3406119A (en)
DE (1)	DE1542261A1 (en)
FR (1)	FR1470723A (en)
GB (1)	GB1126856A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3922379A (en) *	1973-12-17	1975-11-25	Abbott Lab	Microencapsulation process
US4619904A (en) *	1984-10-29	1986-10-28	General Electric Company	Agglutinating immunoassay using protein-coated liquid droplets
US4634681A (en) *	1984-10-29	1987-01-06	General Electric Company	Diagnostic method of determining the presence or absence of select proteins in a liquid sample
US5418010A (en) *	1990-10-05	1995-05-23	Griffith Laboratories Worldwide, Inc.	Microencapsulation process
US6610348B2 (en)	1997-02-17	2003-08-26	Fonterra Tech Limited	Gelling agents and gels containing them
WO2009006792A1 (en) *	2007-07-06	2009-01-15	The University Of Hong Kong	Collagen-based microspheres and methods of preparation and use thereof
EP4035655A1 (en) *	2021-02-01	2022-08-03	Oxford University Innovation Limited	Immune modulating particles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE84710T1 (en) *	1988-06-30	1993-02-15	Centre Nat Rech Scient	PROCESSES FOR THE PRODUCTION OF COLLOIDAL DISPERSABLE PROTEIN SYSTEMS LIKE NANOPARTICLES.

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3137631A (en) *	1959-12-01	1964-06-16	Faberge Inc	Encapsulation in natural products
US3190837A (en) *	1958-12-31	1965-06-22	Ncr Co	Making individual capsules by dual deposition

1965
- 1965-03-05 US US437464A patent/US3406119A/en not_active Expired - Lifetime
1966
- 1966-03-03 DE DE19661542261 patent/DE1542261A1/en active Pending
- 1966-03-04 GB GB9698/66A patent/GB1126856A/en not_active Expired
- 1966-03-04 FR FR52142A patent/FR1470723A/en not_active Expired

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3190837A (en) *	1958-12-31	1965-06-22	Ncr Co	Making individual capsules by dual deposition
US3137631A (en) *	1959-12-01	1964-06-16	Faberge Inc	Encapsulation in natural products

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3922379A (en) *	1973-12-17	1975-11-25	Abbott Lab	Microencapsulation process
US4619904A (en) *	1984-10-29	1986-10-28	General Electric Company	Agglutinating immunoassay using protein-coated liquid droplets
US4634681A (en) *	1984-10-29	1987-01-06	General Electric Company	Diagnostic method of determining the presence or absence of select proteins in a liquid sample
US5418010A (en) *	1990-10-05	1995-05-23	Griffith Laboratories Worldwide, Inc.	Microencapsulation process
US6610348B2 (en)	1997-02-17	2003-08-26	Fonterra Tech Limited	Gelling agents and gels containing them
WO2009006792A1 (en) *	2007-07-06	2009-01-15	The University Of Hong Kong	Collagen-based microspheres and methods of preparation and use thereof
CN101868298B (en) *	2007-07-06	2013-02-06	香港大学	Collagen-based microspheres and methods of preparation and use thereof
EP4035655A1 (en) *	2021-02-01	2022-08-03	Oxford University Innovation Limited	Immune modulating particles

Also Published As

Publication number	Publication date
DE1542261A1 (en)	1970-03-26
FR1470723A (en)	1967-02-24
GB1126856A (en)	1968-09-11

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1982-03-25

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Owner name: SECURITY NATIONAL BANK, A NATIONAL BANKING ASSOCIA