DE2619524A1 - Verfahren zur herstellung von mikrokapseln - Google Patents
Verfahren zur herstellung von mikrokapselnInfo
- Publication number
- DE2619524A1 DE2619524A1 DE19762619524 DE2619524A DE2619524A1 DE 2619524 A1 DE2619524 A1 DE 2619524A1 DE 19762619524 DE19762619524 DE 19762619524 DE 2619524 A DE2619524 A DE 2619524A DE 2619524 A1 DE2619524 A1 DE 2619524A1
- Authority
- DE
- Germany
- Prior art keywords
- microcapsules
- water
- polycarbodiimide
- added
- production
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000003094 microcapsule Substances 0.000 title claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000011162 core material Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- XFLSMWXCZBIXLV-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound CN(C)CCN1CCN(C)CC1 XFLSMWXCZBIXLV-UHFFFAOYSA-N 0.000 description 3
- 230000005501 phase interface Effects 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000011257 shell material Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 description 2
- GGPLWEZGITVTJX-UHFFFAOYSA-N 2,2,4-trimethyl-1,4,2-oxazasilinane Chemical compound CN1CCO[Si](C)(C)C1 GGPLWEZGITVTJX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KTXUOWUHFLBZPW-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)benzene Chemical compound ClC1=CC=CC(C=2C=C(Cl)C=CC=2)=C1 KTXUOWUHFLBZPW-UHFFFAOYSA-N 0.000 description 1
- TXIOGJHPPVXTOY-UHFFFAOYSA-N 1-ethyl-4-methylpiperazine Chemical compound CCN1CCN(C)CC1 TXIOGJHPPVXTOY-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229960002017 echothiophate Drugs 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000008385 outer phase Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229960001147 triclofos Drugs 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- 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
-
- 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]
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762619524 DE2619524A1 (de) | 1976-05-03 | 1976-05-03 | Verfahren zur herstellung von mikrokapseln |
| NL7704327A NL7704327A (nl) | 1976-05-03 | 1977-04-20 | Werkwijze voor het bereiden van microkapsules. |
| US05/791,545 US4119565A (en) | 1976-05-03 | 1977-04-27 | Production of microcapsules, and the resulting microcapsules |
| JP4859977A JPS52133882A (en) | 1976-05-03 | 1977-04-28 | Microcapsule manufacturing method |
| CA277,313A CA1099597A (en) | 1976-05-03 | 1977-04-29 | Production of microcapsules |
| IT49195/77A IT1083154B (it) | 1976-05-03 | 1977-04-29 | Procedimento per produrre microcapsule e prodotto ottenuto |
| CH547277A CH628824A5 (de) | 1976-05-03 | 1977-05-02 | Verfahren zur herstellung von mikrokapseln. |
| GB18308/77A GB1545018A (en) | 1976-05-03 | 1977-05-02 | Production of microcapsules |
| SE7705064A SE7705064L (sv) | 1976-05-03 | 1977-05-02 | Sett att framstella mikrokapslar |
| FR7713383A FR2350137A1 (fr) | 1976-05-03 | 1977-05-03 | Production de microcapsules |
| BE177213A BE854199A (fr) | 1976-05-03 | 1977-05-03 | Production de microcapsules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762619524 DE2619524A1 (de) | 1976-05-03 | 1976-05-03 | Verfahren zur herstellung von mikrokapseln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2619524A1 true DE2619524A1 (de) | 1977-11-24 |
Family
ID=5976952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762619524 Withdrawn DE2619524A1 (de) | 1976-05-03 | 1976-05-03 | Verfahren zur herstellung von mikrokapseln |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4119565A (enExample) |
| JP (1) | JPS52133882A (enExample) |
| BE (1) | BE854199A (enExample) |
| CA (1) | CA1099597A (enExample) |
| CH (1) | CH628824A5 (enExample) |
| DE (1) | DE2619524A1 (enExample) |
| FR (1) | FR2350137A1 (enExample) |
| GB (1) | GB1545018A (enExample) |
| IT (1) | IT1083154B (enExample) |
| NL (1) | NL7704327A (enExample) |
| SE (1) | SE7705064L (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0284933A3 (en) * | 1987-03-31 | 1989-10-18 | Bayer Ag | Foamed microspheres and process for their preparation |
| EP2042534A1 (de) * | 2007-09-28 | 2009-04-01 | Evonik Goldschmidt GmbH | Aminkatalysatoren geeignet zur Herstellung emissionsarmer, rekatalysestabiler Polyurethanweichschaumstoffe |
| EP2628530A1 (de) | 2008-03-11 | 2013-08-21 | Basf Se | Mikrokapseln mit Wänden aus Acylharnstoff |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2617747C2 (de) * | 1976-04-23 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Reaktionsdurchschreibepapiere |
| US4223070A (en) * | 1978-05-04 | 1980-09-16 | Stauffer Chemical Company | Impregnated porous granules with slow release pore membranes and process therefor |
| US4237252A (en) * | 1979-06-28 | 1980-12-02 | Minnesota Mining And Manufacturing Company | Heat activatable one-part liquid resin systems |
| DE3230757A1 (de) * | 1982-08-18 | 1984-02-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von stabilisierten polyisocyanaten, stabilisierte polyisocyanate retardierter reaktivitaet und ihre verwendung zur polyurethanherstellung |
| US5225118A (en) * | 1990-08-15 | 1993-07-06 | Boise Cascade Corporation | Process for manufacturing polyurea microcapsules and product therefrom |
| JP3306131B2 (ja) * | 1992-11-05 | 2002-07-24 | 富士写真フイルム株式会社 | マイクロカプセルの製造方法 |
| EP1203118A1 (en) | 1999-07-19 | 2002-05-08 | Nano-Tex LLC | Nanoparticle-based permanent treatments for textiles |
| DE102004048775A1 (de) * | 2004-10-07 | 2006-04-13 | Degussa Ag | Hoch reaktive uretdiongruppenhaltige Polyurethanzusammensetzungen |
| WO2008077766A1 (de) * | 2006-12-22 | 2008-07-03 | Basf Se | Mikrokapseln, enthaltend verbindungen mit carbodiimidgruppen |
| CN103819497A (zh) * | 2013-05-24 | 2014-05-28 | 江阴斯泰姆生物医药有限公司 | 2,2,4-三甲基-2-硅杂吗啡啉的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853473A (en) * | 1956-08-27 | 1958-09-23 | Du Pont | Production of carbodiimides |
| DE1092007B (de) * | 1959-07-29 | 1960-11-03 | Bayer Ag | Verfahren zur Herstellung von ein Carbodiimid-Isocyanat-Addukt enthaltenden Polyisocyanaten |
| US3432327A (en) * | 1964-03-13 | 1969-03-11 | Pilot Pen Co Ltd | Pressure sensitive copying sheet and the production thereof |
| GB1200432A (en) * | 1968-01-25 | 1970-07-29 | Bayer Ag | Process for the preparation of polyisocyanates which contain a carbodiimideisocyanate adduct |
| ES390653A1 (es) * | 1970-04-28 | 1974-03-16 | Fuji Photo Film Co Ltd | Procedimiento para la produccion de microcapsulas conte- niendo liquido aceitoso. |
| US3677787A (en) * | 1970-10-21 | 1972-07-18 | Us Navy | Method of rehardening encapsulating compositions |
| DE2311712B2 (de) * | 1973-03-09 | 1978-08-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Hersteilung von Mikrokapseln |
| MX146606A (es) * | 1975-05-10 | 1982-07-15 | Bayer Ag | Procedimiento mejorado para preparar la cubierta de una microcapsula |
-
1976
- 1976-05-03 DE DE19762619524 patent/DE2619524A1/de not_active Withdrawn
-
1977
- 1977-04-20 NL NL7704327A patent/NL7704327A/xx not_active Application Discontinuation
- 1977-04-27 US US05/791,545 patent/US4119565A/en not_active Expired - Lifetime
- 1977-04-28 JP JP4859977A patent/JPS52133882A/ja active Pending
- 1977-04-29 IT IT49195/77A patent/IT1083154B/it active
- 1977-04-29 CA CA277,313A patent/CA1099597A/en not_active Expired
- 1977-05-02 SE SE7705064A patent/SE7705064L/xx unknown
- 1977-05-02 GB GB18308/77A patent/GB1545018A/en not_active Expired
- 1977-05-02 CH CH547277A patent/CH628824A5/de not_active IP Right Cessation
- 1977-05-03 BE BE177213A patent/BE854199A/xx not_active IP Right Cessation
- 1977-05-03 FR FR7713383A patent/FR2350137A1/fr active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0284933A3 (en) * | 1987-03-31 | 1989-10-18 | Bayer Ag | Foamed microspheres and process for their preparation |
| EP2042534A1 (de) * | 2007-09-28 | 2009-04-01 | Evonik Goldschmidt GmbH | Aminkatalysatoren geeignet zur Herstellung emissionsarmer, rekatalysestabiler Polyurethanweichschaumstoffe |
| EP2628530A1 (de) | 2008-03-11 | 2013-08-21 | Basf Se | Mikrokapseln mit Wänden aus Acylharnstoff |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1099597A (en) | 1981-04-21 |
| JPS52133882A (en) | 1977-11-09 |
| US4119565A (en) | 1978-10-10 |
| FR2350137A1 (fr) | 1977-12-02 |
| SE7705064L (sv) | 1977-11-04 |
| GB1545018A (en) | 1979-05-02 |
| BE854199A (fr) | 1977-11-03 |
| FR2350137B1 (enExample) | 1982-02-26 |
| IT1083154B (it) | 1985-05-21 |
| NL7704327A (nl) | 1977-11-07 |
| CH628824A5 (de) | 1982-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |