CA2304556C - Method of encapsulated flavors and fragrances by controlled water transport into microcapsules - Google Patents
Method of encapsulated flavors and fragrances by controlled water transport into microcapsules Download PDFInfo
- Publication number
- CA2304556C CA2304556C CA002304556A CA2304556A CA2304556C CA 2304556 C CA2304556 C CA 2304556C CA 002304556 A CA002304556 A CA 002304556A CA 2304556 A CA2304556 A CA 2304556A CA 2304556 C CA2304556 C CA 2304556C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- flavor
- oil
- microcapsule
- fragrance
- 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.)
- Expired - Fee Related
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 74
- 235000019634 flavors Nutrition 0.000 title claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 239000003205 fragrance Substances 0.000 title claims abstract description 66
- 239000003094 microcapsule Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 239000000017 hydrogel Substances 0.000 claims abstract description 25
- 239000003921 oil Substances 0.000 claims description 72
- 235000019198 oils Nutrition 0.000 claims description 72
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- 238000005354 coacervation Methods 0.000 claims description 13
- 230000000717 retained effect Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 11
- 239000008158 vegetable oil Substances 0.000 claims description 11
- 238000004132 cross linking Methods 0.000 claims description 10
- 150000001720 carbohydrates Chemical class 0.000 claims description 7
- 238000009792 diffusion process Methods 0.000 claims description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- 229920001059 synthetic polymer Polymers 0.000 claims description 6
- 235000010446 mineral oil Nutrition 0.000 claims description 5
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims 1
- 239000002775 capsule Substances 0.000 abstract description 40
- 238000005192 partition Methods 0.000 abstract description 11
- 239000000243 solution Substances 0.000 description 40
- 239000011162 core material Substances 0.000 description 27
- 239000012071 phase Substances 0.000 description 23
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 150000002632 lipids Chemical class 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 238000013019 agitation Methods 0.000 description 11
- 108010010803 Gelatin Proteins 0.000 description 10
- 239000008273 gelatin Substances 0.000 description 10
- 229920000159 gelatin Polymers 0.000 description 10
- 235000019322 gelatine Nutrition 0.000 description 10
- 235000011852 gelatine desserts Nutrition 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000000084 colloidal system Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000007667 floating Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 239000004299 sodium benzoate Substances 0.000 description 3
- 235000010234 sodium benzoate Nutrition 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229940013317 fish oils Drugs 0.000 description 2
- 238000005188 flotation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 238000011176 pooling Methods 0.000 description 2
- 238000012802 pre-warming Methods 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 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 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 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 description 1
- 108060008539 Transglutaminase Proteins 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000008239 natural water Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- -1 silica compound Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 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 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
- B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles
-
- 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]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Fats And Perfumes (AREA)
- General Preparation And Processing Of Foods (AREA)
- Seasonings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/947,694 US6045835A (en) | 1997-10-08 | 1997-10-08 | Method of encapsulating flavors and fragrances by controlled water transport into microcapsules |
| US08/947,694 | 1997-10-08 | ||
| PCT/IB1998/001551 WO1999017871A1 (en) | 1997-10-08 | 1998-10-05 | Method of encapsulated flavors and fragrances by controlled water transport into microcapsules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2304556A1 CA2304556A1 (en) | 1999-04-15 |
| CA2304556C true CA2304556C (en) | 2004-05-25 |
Family
ID=25486597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002304556A Expired - Fee Related CA2304556C (en) | 1997-10-08 | 1998-10-05 | Method of encapsulated flavors and fragrances by controlled water transport into microcapsules |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6045835A (enExample) |
| EP (1) | EP1027147B1 (enExample) |
| JP (1) | JP3616009B2 (enExample) |
| CN (1) | CN1118319C (enExample) |
| AT (1) | ATE217804T1 (enExample) |
| AU (1) | AU744495B2 (enExample) |
| BR (1) | BR9812887A (enExample) |
| CA (1) | CA2304556C (enExample) |
| DE (1) | DE69805537T2 (enExample) |
| ES (1) | ES2175771T3 (enExample) |
| PL (1) | PL339768A1 (enExample) |
| TR (1) | TR200000959T2 (enExample) |
| WO (1) | WO1999017871A1 (enExample) |
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6106875A (en) * | 1997-10-08 | 2000-08-22 | Givaudan Roure (International) Sa | Method of encapsulating flavors and fragrances by controlled water transport into microcapsules |
| US6958148B1 (en) | 1998-01-20 | 2005-10-25 | Pericor Science, Inc. | Linkage of agents to body tissue using microparticles and transglutaminase |
| KR100541753B1 (ko) * | 1999-07-27 | 2006-01-10 | 가부시키가이샤 시세이도 | 마이크로캡슐 및 그 제조방법 |
| US6750978B1 (en) * | 2000-04-27 | 2004-06-15 | Leapfrog Enterprises, Inc. | Print media information system with a portable print media receiving unit assembly |
| JP2004509739A (ja) | 2000-09-27 | 2004-04-02 | ベリオン インコーポレイテッド | 即時水溶解性カプセルおよびその製法 |
| JP2005522991A (ja) * | 2001-11-16 | 2005-08-04 | ジボダン エス エー | 可食性フィルム |
| WO2004034791A1 (en) * | 2002-10-21 | 2004-04-29 | Givaudan Sa | Pesticidal compositions |
| US20030194416A1 (en) * | 2002-04-15 | 2003-10-16 | Adl Shefer | Moisture triggered release systems comprising aroma ingredients providing fragrance burst in response to moisture |
| US20030203075A1 (en) * | 2002-04-25 | 2003-10-30 | Taylor Lee Richard | Flavored straw inserts |
| US7335631B2 (en) * | 2002-09-09 | 2008-02-26 | Symrise, Inc. | Encapsulated perfume compositions in hair and skin products which release a burst of fragrance after initial topical application |
| US20040191444A1 (en) * | 2003-03-24 | 2004-09-30 | Hetzner Jess Lee | Scented chemical storage container |
| GB0310673D0 (en) * | 2003-05-09 | 2003-06-11 | Givaudan Sa | Alginate matrix particles |
| US20050112152A1 (en) * | 2003-11-20 | 2005-05-26 | Popplewell Lewis M. | Encapsulated materials |
| US20080300314A1 (en) * | 2003-11-21 | 2008-12-04 | Givaudan Sa | Cooling Compounds |
| CA2488981C (en) | 2003-12-15 | 2008-06-17 | Rohm And Haas Company | Oil absorbing composition and process |
| EP1632281B1 (en) | 2003-12-15 | 2011-09-14 | Rohm And Haas Company | Process for absorbing hydrophobic substances in polymers having an hollow structure |
| EP1814975A1 (en) * | 2004-11-29 | 2007-08-08 | Givaudan SA | Substrate care product |
| PL1841521T3 (pl) * | 2005-01-25 | 2013-07-31 | Givaudan Sa | Sposób kapsułkowania związków |
| WO2006119660A1 (en) * | 2005-05-11 | 2006-11-16 | Givaudan Sa | Encapsulation method |
| BRPI0616821B1 (pt) * | 2005-08-15 | 2022-06-07 | Givaudan Sa | Método para proporcionar um efeito refrescante em um produto e produto possuindo um efeito refrescante |
| US20090098066A1 (en) * | 2005-08-22 | 2009-04-16 | Galopin Christophe C | Substituted bicyclo [2.2.2] oct/5-ene compounds and their use as cooling agents |
| WO2007048265A1 (en) * | 2005-10-25 | 2007-05-03 | Givaudan Sa | Organic compounds |
| US7810507B2 (en) * | 2006-02-10 | 2010-10-12 | R. J. Reynolds Tobacco Company | Smokeless tobacco composition |
| BRPI0709393A2 (pt) * | 2006-03-15 | 2011-07-05 | Givaudan Sa | compostos 2-alcoxifenóis para -substituìdos, uso dos mesmos, método de fornecer um efeito refrescante à boca ou pele e produto contendo ditos compostos |
| US20110097449A1 (en) * | 2006-06-30 | 2011-04-28 | Conagra Foods Rdm, Inc. | Seasoning and method for seasoning a food product while reducing dietary sodium intake |
| CN101516492B (zh) * | 2006-09-12 | 2013-02-20 | 奇华顿股份有限公司 | 胶囊 |
| MX2009003329A (es) * | 2006-09-27 | 2009-07-31 | Conagra Foods Rdm Inc | Sazonador y metodo para mejorar y potenciar el sabor de un alimento utilizando microencapsulacion. |
| US8357318B2 (en) * | 2007-05-08 | 2013-01-22 | Givaudan S.A. | Wax encapsulation |
| WO2008151460A2 (en) | 2007-06-13 | 2008-12-18 | Givaudan Sa | Cooling compounds |
| US7880011B2 (en) * | 2007-07-23 | 2011-02-01 | Givandan, S.A. | Amide addition reaction |
| CN101873809B (zh) | 2007-07-23 | 2014-11-12 | R.J.雷诺兹烟草公司 | 无烟烟草组合物 |
| GB0724739D0 (en) * | 2007-12-20 | 2008-01-30 | Unilever Plc | Improvements relating to fabric treatment compositions |
| WO2009089641A1 (en) * | 2008-01-17 | 2009-07-23 | Givaudan Sa | Benzimidazole derivatives and their use as cooling agents |
| ES2610627T3 (es) | 2008-10-27 | 2017-04-28 | Unilever N.V. | Composiciones antitranspirantes o desodorantes |
| ES2618314T3 (es) | 2008-10-27 | 2017-06-21 | Unilever N.V. | Composiciones antitranspirantes |
| EP2181692B1 (en) | 2008-10-27 | 2016-09-28 | Unilever PLC | Antiperspirant compositions |
| CA2742367A1 (en) * | 2008-11-10 | 2010-05-14 | Colgate-Palmolive Company | Shelf stable capsules |
| EP2204155A1 (en) | 2008-12-30 | 2010-07-07 | Takasago International Corporation | Fragrance composition for core shell microcapsules |
| WO2010128026A2 (en) | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
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-
1997
- 1997-10-08 US US08/947,694 patent/US6045835A/en not_active Expired - Lifetime
-
1998
- 1998-10-05 AT AT98944179T patent/ATE217804T1/de not_active IP Right Cessation
- 1998-10-05 CN CN98809968A patent/CN1118319C/zh not_active Expired - Lifetime
- 1998-10-05 JP JP2000514732A patent/JP3616009B2/ja not_active Expired - Lifetime
- 1998-10-05 EP EP98944179A patent/EP1027147B1/en not_active Expired - Lifetime
- 1998-10-05 TR TR2000/00959T patent/TR200000959T2/xx unknown
- 1998-10-05 DE DE69805537T patent/DE69805537T2/de not_active Expired - Lifetime
- 1998-10-05 WO PCT/IB1998/001551 patent/WO1999017871A1/en not_active Ceased
- 1998-10-05 BR BR9812887-6A patent/BR9812887A/pt not_active Application Discontinuation
- 1998-10-05 PL PL98339768A patent/PL339768A1/xx unknown
- 1998-10-05 ES ES98944179T patent/ES2175771T3/es not_active Expired - Lifetime
- 1998-10-05 CA CA002304556A patent/CA2304556C/en not_active Expired - Fee Related
- 1998-10-05 AU AU91817/98A patent/AU744495B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JP3616009B2 (ja) | 2005-02-02 |
| WO1999017871A1 (en) | 1999-04-15 |
| EP1027147A1 (en) | 2000-08-16 |
| PL339768A1 (en) | 2001-01-02 |
| BR9812887A (pt) | 2000-08-08 |
| ATE217804T1 (de) | 2002-06-15 |
| EP1027147B1 (en) | 2002-05-22 |
| AU744495B2 (en) | 2002-02-28 |
| CA2304556A1 (en) | 1999-04-15 |
| CN1285768A (zh) | 2001-02-28 |
| CN1118319C (zh) | 2003-08-20 |
| TR200000959T2 (tr) | 2000-10-23 |
| JP2004513187A (ja) | 2004-04-30 |
| DE69805537D1 (de) | 2002-06-27 |
| US6045835A (en) | 2000-04-04 |
| ES2175771T3 (es) | 2002-11-16 |
| DE69805537T2 (de) | 2002-12-05 |
| AU9181798A (en) | 1999-04-27 |
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