CH496472A - Procédé de préparation de petites capsules polymères - Google Patents
Procédé de préparation de petites capsules polymèresInfo
- Publication number
- CH496472A CH496472A CH149369A CH149369A CH496472A CH 496472 A CH496472 A CH 496472A CH 149369 A CH149369 A CH 149369A CH 149369 A CH149369 A CH 149369A CH 496472 A CH496472 A CH 496472A
- Authority
- CH
- Switzerland
- Prior art keywords
- capsules
- solution
- aqueous solution
- poly
- walls
- Prior art date
Links
- 239000003094 microcapsule Substances 0.000 title abstract 2
- 229920001477 hydrophilic polymer Polymers 0.000 title description 3
- 239000002861 polymer material Substances 0.000 title description 2
- 239000007900 aqueous suspension Substances 0.000 title 1
- 239000002775 capsule Substances 0.000 claims abstract description 62
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 25
- 239000002245 particle Substances 0.000 claims abstract description 22
- 230000008569 process Effects 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000005191 phase separation Methods 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims description 45
- 239000000126 substance Substances 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 36
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 22
- 239000003981 vehicle Substances 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 11
- 229940074391 gallic acid Drugs 0.000 claims description 11
- 235000004515 gallic acid Nutrition 0.000 claims description 11
- 229920000084 Gum arabic Polymers 0.000 claims description 10
- 239000000205 acacia gum Substances 0.000 claims description 10
- 235000010489 acacia gum Nutrition 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 9
- 229960001553 phloroglucinol Drugs 0.000 claims description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 9
- 235000011152 sodium sulphate Nutrition 0.000 claims description 9
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- COVFEVWNJUOYRL-UHFFFAOYSA-N digallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 COVFEVWNJUOYRL-UHFFFAOYSA-N 0.000 claims description 6
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 claims description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 6
- 229960001755 resorcinol Drugs 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 5
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- -1 vanadyl dihydrate-sulphate Chemical compound 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000008098 formaldehyde solution Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004101 4-Hexylresorcinol Substances 0.000 claims description 3
- WFJIVOKAWHGMBH-UHFFFAOYSA-N 4-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 claims description 3
- 235000019360 4-hexylresorcinol Nutrition 0.000 claims description 3
- 229920002707 Digallic acid Polymers 0.000 claims description 3
- 239000001263 FEMA 3042 Substances 0.000 claims description 3
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229960003258 hexylresorcinol Drugs 0.000 claims description 3
- 239000011344 liquid material Substances 0.000 claims description 3
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 claims description 3
- 229940079877 pyrogallol Drugs 0.000 claims description 3
- 239000011343 solid material Substances 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 3
- 235000015523 tannic acid Nutrition 0.000 claims description 3
- 229920002258 tannic acid Polymers 0.000 claims description 3
- 229940033123 tannic acid Drugs 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical group [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 claims description 3
- 229940041260 vanadyl sulfate Drugs 0.000 claims description 3
- 229910000352 vanadyl sulfate Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000008135 aqueous vehicle Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229920001339 phlorotannin Polymers 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 241000978776 Senegalia senegal Species 0.000 claims 2
- 230000002349 favourable effect Effects 0.000 claims 1
- 238000005538 encapsulation Methods 0.000 abstract description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 3
- 230000003115 biocidal effect Effects 0.000 abstract description 2
- 239000003337 fertilizer Substances 0.000 abstract description 2
- 239000002657 fibrous material Substances 0.000 abstract description 2
- 239000011521 glass Substances 0.000 abstract description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- 239000002480 mineral oil Substances 0.000 abstract description 2
- 239000002304 perfume Substances 0.000 abstract description 2
- 239000000049 pigment Substances 0.000 abstract description 2
- 229920002994 synthetic fiber Polymers 0.000 abstract description 2
- 239000008157 edible vegetable oil Substances 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000007791 liquid phase Substances 0.000 description 12
- 244000215068 Acacia senegal Species 0.000 description 8
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 7
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical group CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 7
- 239000011162 core material Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 125000005287 vanadyl group Chemical group 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 239000007771 core particle Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- IBHWREHFNDMRPR-UHFFFAOYSA-N phloroglucinol carboxylic acid Natural products OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- Ignition Installations For Internal Combustion Engines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70112868A | 1968-01-29 | 1968-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH496472A true CH496472A (fr) | 1970-09-30 |
Family
ID=24816183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149369A CH496472A (fr) | 1968-01-29 | 1969-01-29 | Procédé de préparation de petites capsules polymères |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT291940B (OSRAM) |
| BE (1) | BE727294A (OSRAM) |
| BR (1) | BR6905912D0 (OSRAM) |
| CH (1) | CH496472A (OSRAM) |
| DK (1) | DK125742B (OSRAM) |
| FR (1) | FR1596380A (OSRAM) |
| GB (1) | GB1198412A (OSRAM) |
| NL (1) | NL152178B (OSRAM) |
| NO (1) | NO124519B (OSRAM) |
| SE (1) | SE344686B (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4525520A (en) * | 1983-03-28 | 1985-06-25 | Kanzaki Paper Manufacturing Company, Ltd. | Method of preparing microcapsules |
| US4777089A (en) * | 1985-05-08 | 1988-10-11 | Lion Corporation | Microcapsule containing hydrous composition |
| US4908233A (en) * | 1985-05-08 | 1990-03-13 | Lion Corporation | Production of microcapsules by simple coacervation |
| US6974592B2 (en) | 2002-04-11 | 2005-12-13 | Ocean Nutrition Canada Limited | Encapsulated agglomeration of microcapsules and method for the preparation thereof |
| JP4833553B2 (ja) | 2002-11-04 | 2011-12-07 | オーシャン・ニュートリション・カナダ・リミテッド | 複数の殻を有するマイクロカプセル及びそれらの調製方法 |
| US8034450B2 (en) | 2005-01-21 | 2011-10-11 | Ocean Nutrition Canada Limited | Microcapsules and emulsions containing low bloom gelatin and methods of making and using thereof |
| US9968120B2 (en) | 2006-05-17 | 2018-05-15 | Dsm Nutritional Products Ag | Homogenized formulations containing microcapsules and methods of making and using thereof |
| CA2654031C (en) | 2006-06-05 | 2016-05-24 | Ocean Nutrition Canada Limited | Microcapsules with improved shells |
| WO2008085997A2 (en) | 2007-01-10 | 2008-07-17 | Ocean Nutrition Canada, Ltd. | Vegetarian microcapsules |
| RS59685B1 (sr) | 2015-07-30 | 2020-01-31 | Doehler Gmbh | Guma arabika od acacia seyal |
-
1968
- 1968-12-19 SE SE1746468A patent/SE344686B/xx unknown
- 1968-12-24 FR FR1596380D patent/FR1596380A/fr not_active Expired
-
1969
- 1969-01-02 NO NO569A patent/NO124519B/no unknown
- 1969-01-07 GB GB94569A patent/GB1198412A/en not_active Expired
- 1969-01-23 BE BE727294D patent/BE727294A/xx unknown
- 1969-01-27 AT AT78469A patent/AT291940B/de not_active IP Right Cessation
- 1969-01-28 NL NL6901366A patent/NL152178B/xx not_active IP Right Cessation
- 1969-01-28 BR BR20591269A patent/BR6905912D0/pt unknown
- 1969-01-28 DK DK44869A patent/DK125742B/da not_active IP Right Cessation
- 1969-01-29 CH CH149369A patent/CH496472A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR6905912D0 (pt) | 1973-02-08 |
| SE344686B (OSRAM) | 1972-05-02 |
| NO124519B (OSRAM) | 1972-05-02 |
| NL6901366A (OSRAM) | 1969-07-31 |
| GB1198412A (en) | 1970-07-15 |
| BE727294A (OSRAM) | 1969-07-01 |
| NL152178B (nl) | 1977-02-15 |
| FR1596380A (OSRAM) | 1970-06-15 |
| DK125742B (da) | 1973-04-30 |
| AT291940B (de) | 1971-08-10 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: EURAND AMERICA, INCORPORATED |
|
| PL | Patent ceased |