DE19646110A1 - Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten - Google Patents
Mikrokapseln unter Verwendung von Iminooxadiazindion-PolyisocyanatenInfo
- Publication number
- DE19646110A1 DE19646110A1 DE19646110A DE19646110A DE19646110A1 DE 19646110 A1 DE19646110 A1 DE 19646110A1 DE 19646110 A DE19646110 A DE 19646110A DE 19646110 A DE19646110 A DE 19646110A DE 19646110 A1 DE19646110 A1 DE 19646110A1
- Authority
- DE
- Germany
- Prior art keywords
- isocyanates
- formula
- microcapsules
- weight
- isocyanate
- 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- Withdrawn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
- 239000003094 microcapsule Substances 0.000 title claims description 41
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 title claims description 8
- 239000005056 polyisocyanate Substances 0.000 title description 16
- 229920001228 polyisocyanate Polymers 0.000 title description 16
- 239000012948 isocyanate Substances 0.000 claims description 62
- 150000002513 isocyanates Chemical class 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 31
- 239000000839 emulsion Substances 0.000 claims description 28
- 239000003921 oil Substances 0.000 claims description 28
- 239000004971 Cross linker Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 claims description 9
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical group NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 claims description 9
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003925 fat Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 150000004074 biphenyls Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 125000005498 phthalate group Chemical class 0.000 claims description 2
- 238000004581 coalescence Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 31
- 239000002775 capsule Substances 0.000 description 30
- 239000006185 dispersion Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- 239000003086 colorant Substances 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 14
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 10
- 229920002451 polyvinyl alcohol Polymers 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000005538 encapsulation Methods 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000001913 cyanates Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical class C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- FXSFKECPPGDGBN-UHFFFAOYSA-N 3,3-bis(1h-indol-2-yl)-2-benzofuran-1-one Chemical class C12=CC=CC=C2C(=O)OC1(C=1NC2=CC=CC=C2C=1)C1=CC2=CC=CC=C2N1 FXSFKECPPGDGBN-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- KEZMBAQUUXDDDQ-UHFFFAOYSA-N CCC.N=C=O.N=C=O Chemical compound CCC.N=C=O.N=C=O KEZMBAQUUXDDDQ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical class N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 1
- CLWKGFMSGOQXNJ-UHFFFAOYSA-N N=C=O.N=C=O.CCC1(CC)CCCCC1C Chemical compound N=C=O.N=C=O.CCC1(CC)CCCCC1C CLWKGFMSGOQXNJ-UHFFFAOYSA-N 0.000 description 1
- QCJBVWNJRIOSDN-UHFFFAOYSA-N N=C=O.N=C=O.CCC1CCCCC1 Chemical class N=C=O.N=C=O.CCC1CCCCC1 QCJBVWNJRIOSDN-UHFFFAOYSA-N 0.000 description 1
- LAGMANKZFBMQGW-UHFFFAOYSA-N N=C=O.N=C=O.CCCC Chemical class N=C=O.N=C=O.CCCC LAGMANKZFBMQGW-UHFFFAOYSA-N 0.000 description 1
- TXQHYIKVGQIJAM-UHFFFAOYSA-N N=C=O.N=C=O.CCCCC Chemical class N=C=O.N=C=O.CCCCC TXQHYIKVGQIJAM-UHFFFAOYSA-N 0.000 description 1
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical class N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 1
- OEMVAFGEQGKIOR-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCC Chemical class N=C=O.N=C=O.CCCCCCCC OEMVAFGEQGKIOR-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KFSZGBHNIHLIAA-UHFFFAOYSA-M benzyl(trimethyl)azanium;fluoride Chemical compound [F-].C[N+](C)(C)CC1=CC=CC=C1 KFSZGBHNIHLIAA-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical class CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- STBLQDMGPBQTMI-UHFFFAOYSA-N heptane;isocyanic acid Chemical class N=C=O.N=C=O.CCCCCCC STBLQDMGPBQTMI-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WPRDEDGZJLTOFJ-UHFFFAOYSA-N oxadiazin-4-imine Chemical compound N=C1C=CON=N1 WPRDEDGZJLTOFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
-
- 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)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Polyurethanes Or Polyureas (AREA)
- Color Printing (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19646110A DE19646110A1 (de) | 1996-11-08 | 1996-11-08 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
| TW086113943A TW341526B (en) | 1996-11-08 | 1997-09-25 | Microcapsules using iminooxadiazinedione polyisocyanates |
| IN2903DE1997 IN186809B (enExample) | 1996-11-08 | 1997-10-09 | |
| US08/956,821 US6020066A (en) | 1996-11-08 | 1997-10-23 | Microcapsules using iminooxadiazinedione polyisocyanates |
| ES97118626T ES2157509T3 (es) | 1996-11-08 | 1997-10-27 | Microcapsulas con empleo de iminooxadiazindiona-poliisocianatos. |
| DE59703664T DE59703664D1 (de) | 1996-11-08 | 1997-10-27 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
| PT97118626T PT841088E (pt) | 1996-11-08 | 1997-10-27 | Microcapsulas produzidas mediante uso de poli-isocianatos de imino-oxadiazinodiona |
| EP97118626A EP0841088B1 (de) | 1996-11-08 | 1997-10-27 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
| JP9315901A JPH10137578A (ja) | 1996-11-08 | 1997-10-31 | イミノオキサジアジンジオンポリイソシアネートを用いるマイクロカプセル |
| ARP970105196A AR010555A1 (es) | 1996-11-08 | 1997-11-07 | Microcapsulas que tienen sus paredes constituidas por productos de reaccion de reticulantes con grupos nh2 con isocianatos, procedimiento para su obtencion y papeles de calco exentos de carbon. |
| ZA9710042A ZA9710042B (en) | 1996-11-08 | 1997-11-07 | Microcapsules using iminooxadiazinedione polyisocyanates. |
| MXPA/A/1997/008588A MXPA97008588A (en) | 1996-11-08 | 1997-11-07 | Microcapsules with employment of iminooxadiazindiona-poliisociana |
| CN97122266A CN1100602C (zh) | 1996-11-08 | 1997-11-07 | 使用亚氨基噁二嗪二酮多异氰酸酯的微胶囊 |
| IDP973626A ID18090A (id) | 1996-11-08 | 1997-11-07 | Mikrokapsul menggunakan iminooksadiazinadiona poliisosianat |
| BR9705447-0A BR9705447A (pt) | 1996-11-08 | 1997-11-07 | Microcápsulas usando poliisocianatos de iminooxadiazinadiona |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19646110A DE19646110A1 (de) | 1996-11-08 | 1996-11-08 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19646110A1 true DE19646110A1 (de) | 1998-05-14 |
Family
ID=7811048
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19646110A Withdrawn DE19646110A1 (de) | 1996-11-08 | 1996-11-08 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
| DE59703664T Expired - Lifetime DE59703664D1 (de) | 1996-11-08 | 1997-10-27 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59703664T Expired - Lifetime DE59703664D1 (de) | 1996-11-08 | 1997-10-27 | Mikrokapseln unter Verwendung von Iminooxadiazindion-Polyisocyanaten |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6020066A (enExample) |
| EP (1) | EP0841088B1 (enExample) |
| JP (1) | JPH10137578A (enExample) |
| CN (1) | CN1100602C (enExample) |
| AR (1) | AR010555A1 (enExample) |
| BR (1) | BR9705447A (enExample) |
| DE (2) | DE19646110A1 (enExample) |
| ES (1) | ES2157509T3 (enExample) |
| ID (1) | ID18090A (enExample) |
| IN (1) | IN186809B (enExample) |
| PT (1) | PT841088E (enExample) |
| TW (1) | TW341526B (enExample) |
| ZA (1) | ZA9710042B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008002145A1 (de) | 2008-06-02 | 2009-12-03 | Symrise Gmbh & Co. Kg | Kapsel mit organisch-anorganischer Hybridwand |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT962454E (pt) * | 1998-06-02 | 2002-12-31 | Bayer Ag | Processo para a preparacao de poli-isocianatos contendo grupos imino-oxadiazinodiona produtos do processo assim preparados e sua utilizacao |
| DE19840583A1 (de) * | 1998-09-05 | 2000-03-09 | Bayer Ag | Mikrokapsel-Formulierungen |
| DE19840582A1 (de) * | 1998-09-05 | 2000-03-09 | Bayer Ag | Mikrokapsel-Formulierungen |
| US6653256B1 (en) | 1999-08-24 | 2003-11-25 | Bayer Aktiengesellschaft | Microcapsule formulations |
| DK1292386T3 (da) | 2000-06-05 | 2006-03-27 | Syngenta Ltd | Hidtil ukendte mikrokapsler |
| DE10051194A1 (de) * | 2000-10-16 | 2002-04-25 | Bayer Ag | Mikrokapseln mit Wänden aus Polyharnstoff |
| DE10051190A1 (de) * | 2000-10-16 | 2002-04-25 | Bayer Ag | Mikrokapseln mit Wänden aus Polyharnstoff |
| DE10117671A1 (de) * | 2001-04-09 | 2002-10-10 | Bayer Ag | Mit duftstoffhaltigen Mikrokapseln ausgerüstetes Leder |
| JP4463548B2 (ja) * | 2001-07-12 | 2010-05-19 | リアクサ・リミテッド | マイクロカプセル化触媒、及びその製造法と使用法 |
| DE10241000A1 (de) * | 2001-09-10 | 2003-03-27 | Bayer Ag | Mikrokapsel-haltige Vliese |
| GB0128839D0 (en) * | 2001-12-01 | 2002-01-23 | Univ Cambridge Tech | Encapsulated transition metal reagents for reactions in supercritical carbon dioxide |
| US20040137031A1 (en) * | 2002-12-13 | 2004-07-15 | Monsanto Technology Llc | Microcapsules with amine adjusted release rates |
| CN101098953B (zh) | 2004-04-09 | 2011-03-09 | 荷兰联合利华有限公司 | 在洗涤产品中使用的颗粒剂及其制造方法 |
| AU2005253972A1 (en) * | 2004-06-14 | 2005-12-29 | Monsanto Technology Llc | Microcapsules having activated release of core material therein |
| WO2006066654A1 (en) * | 2004-12-23 | 2006-06-29 | Unilever Plc | Liquid detergent compositions and their use |
| GB0524659D0 (en) * | 2005-12-02 | 2006-01-11 | Unilever Plc | Improvements relating to fabric treatment compositions |
| JP4739995B2 (ja) * | 2006-03-10 | 2011-08-03 | Ｊｘ日鉱日石エネルギー株式会社 | 感圧記録材料用マイクロカプセルとその製造方法及びそれを用いた感圧記録材料 |
| PL2169042T3 (pl) * | 2008-09-30 | 2012-09-28 | Procter & Gamble | Kompozycja zawierająca mikrokapsułki |
| MX2011004847A (es) | 2008-11-07 | 2011-05-30 | Procter & Gamble | Agente benefico que contiene particulas de suministro. |
| MX339903B (es) | 2009-02-13 | 2016-06-15 | Monsanto Technology Llc | Encapsulacion de herbicidas para reducir daños en cultivos. |
| GB0902634D0 (en) | 2009-02-18 | 2009-04-01 | Reaxa Ltd | Microencapsulated catalyst |
| EP2336286A1 (en) | 2009-12-18 | 2011-06-22 | The Procter & Gamble Company | Composition comprising microcapsules |
| EP2336285B1 (en) | 2009-12-18 | 2013-09-04 | The Procter & Gamble Company | Composition comprising microcapsules |
| WO2011120772A1 (en) | 2010-03-31 | 2011-10-06 | Unilever Plc | Microcapsule incorporation in structured liquid detergents |
| EP2553072B1 (en) | 2010-04-01 | 2015-05-06 | Unilever PLC | Structuring detergent liquids with hydrogenated castor oil |
| BR112013004485B1 (pt) | 2010-08-18 | 2022-02-08 | Monsanto Technology Llc | Método para controle de ervas daninhas em campo de plantas de cultura |
| FR2965190B1 (fr) * | 2010-09-24 | 2013-12-27 | Univ Tours Francois Rabelais | Procede de fabrication de microcapsules polysiloxane fonctionnalisees et peu poreuses. |
| CN102146219B (zh) * | 2011-01-19 | 2013-04-24 | 山西大学 | 活性染料微胶囊的制备方法 |
| US8936030B2 (en) | 2011-03-25 | 2015-01-20 | Katherine Rose Kovarik | Nail polish remover method and device |
| EP2495300A1 (en) | 2011-03-04 | 2012-09-05 | Unilever Plc, A Company Registered In England And Wales under company no. 41424 of Unilever House | Structuring detergent liquids with hydrogenated castor oil |
| US12245673B2 (en) | 2011-03-25 | 2025-03-11 | Seed Health, Inc. | Insect repellent pet collar |
| BR112014026300A2 (pt) | 2012-04-23 | 2017-06-27 | Unilever Nv | composição de detergente para lavanderia líquida, isotrópica, aquosa, externamente estruturada |
| WO2013160022A1 (en) | 2012-04-23 | 2013-10-31 | Unilever Plc | Externally structured aqueous isotropic liquid detergent compositions |
| CN104271724B (zh) | 2012-04-23 | 2017-02-15 | 荷兰联合利华有限公司 | 外部结构化的水性各向同性液体洗涤剂组合物 |
| US20150037565A1 (en) * | 2013-07-31 | 2015-02-05 | P.H. Glatfelter Company | Tamper evident documents and inks |
| US9221989B2 (en) * | 2013-08-28 | 2015-12-29 | P.H. Glatfelter Company | Tamper evident documents and inks |
| EP2839877A1 (de) | 2013-08-21 | 2015-02-25 | Kwizda Agro GmbH | Verfahren zur Herstellung von Konzentraten von vorzugsweise wasserlöslichen Wirkstoffen |
| UY40114A (es) | 2014-01-27 | 2023-02-28 | Monsanto Technology Llc | Composiciones herbicidas concentradas acuosas que contienen microcápsulas (acetocloro), fomesafen, un espesante pseudoplástico y un agente rompedor de estructuras (urea) |
| CN106400589B (zh) * | 2016-08-30 | 2018-09-28 | 苏州丰倍生物科技有限公司 | 一种环保型无碳复写纸压敏油的制备方法 |
| EP3625320A1 (en) | 2017-05-15 | 2020-03-25 | Unilever PLC | Composition |
| WO2018210524A1 (en) | 2017-05-15 | 2018-11-22 | Unilever Plc | Composition |
| WO2018210522A1 (en) | 2017-05-15 | 2018-11-22 | Unilever Plc | Composition |
| WO2018210523A1 (en) | 2017-05-15 | 2018-11-22 | Unilever Plc | Composition |
| US10464948B2 (en) | 2017-05-30 | 2019-11-05 | Covestro Deutschland Ag | Polycyclic diiminooxadiazinones |
| WO2018231913A1 (en) | 2017-06-13 | 2018-12-20 | Monsanto Technology Llc | Microencapsulated herbicides |
| SG10201806031VA (en) * | 2018-07-13 | 2020-02-27 | Mitsui Chemicals Inc | Re-dispersible polyurea microcapsules and method of preparing re-dispersible polyurea microcapsules |
| UA129154C2 (uk) | 2019-01-30 | 2025-01-29 | Монсанто Текнолоджі Ллс | Мікрокапсульовані ацетамідні гербіциди |
| EP4339121A1 (en) | 2022-09-14 | 2024-03-20 | The Procter & Gamble Company | Consumer product |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2909950A1 (de) * | 1979-03-14 | 1980-10-02 | Bayer Ag | Mikrokapseln |
| DE2909906A1 (de) * | 1979-03-14 | 1980-10-02 | Bayer Ag | Verfahren zur kontinuierlichen herstellung von mikrokapseln |
| DE3421865A1 (de) * | 1984-06-13 | 1985-12-19 | Bayer Ag, 5090 Leverkusen | Kontinuierliche herstellung von mikrokapseldispersionen |
| FR2591124B1 (fr) * | 1985-12-10 | 1988-02-12 | Rhone Poulenc Spec Chim | Procede de microencapsulation par polyaddition-interfaciale. |
| DE3902078A1 (de) * | 1989-01-25 | 1990-07-26 | Bayer Ag | Verfahren zur herstellung von modifizierten, isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
| US5164126A (en) * | 1991-03-05 | 1992-11-17 | Appleton Papers Inc. | Process for microencapsulation |
| DE19532060A1 (de) * | 1995-08-31 | 1997-03-06 | Bayer Ag | Polycyclische Iminooxadiazindione, deren Herstellung und Verwendung |
| DE19607632A1 (de) * | 1996-02-29 | 1997-09-04 | Bayer Ag | Mikrokapseln mit Wänden aus Umsetzungsprodukten von Biuret-Polyisocyanaten und Guanidinen |
-
1996
- 1996-11-08 DE DE19646110A patent/DE19646110A1/de not_active Withdrawn
-
1997
- 1997-09-25 TW TW086113943A patent/TW341526B/zh active
- 1997-10-09 IN IN2903DE1997 patent/IN186809B/en unknown
- 1997-10-23 US US08/956,821 patent/US6020066A/en not_active Expired - Fee Related
- 1997-10-27 EP EP97118626A patent/EP0841088B1/de not_active Expired - Lifetime
- 1997-10-27 DE DE59703664T patent/DE59703664D1/de not_active Expired - Lifetime
- 1997-10-27 PT PT97118626T patent/PT841088E/pt unknown
- 1997-10-27 ES ES97118626T patent/ES2157509T3/es not_active Expired - Lifetime
- 1997-10-31 JP JP9315901A patent/JPH10137578A/ja active Pending
- 1997-11-07 CN CN97122266A patent/CN1100602C/zh not_active Expired - Fee Related
- 1997-11-07 ZA ZA9710042A patent/ZA9710042B/xx unknown
- 1997-11-07 AR ARP970105196A patent/AR010555A1/es unknown
- 1997-11-07 ID IDP973626A patent/ID18090A/id unknown
- 1997-11-07 BR BR9705447-0A patent/BR9705447A/pt not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008002145A1 (de) | 2008-06-02 | 2009-12-03 | Symrise Gmbh & Co. Kg | Kapsel mit organisch-anorganischer Hybridwand |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0841088A2 (de) | 1998-05-13 |
| DE59703664D1 (de) | 2001-07-05 |
| TW341526B (en) | 1998-10-01 |
| BR9705447A (pt) | 2000-02-29 |
| EP0841088B1 (de) | 2001-05-30 |
| US6020066A (en) | 2000-02-01 |
| PT841088E (pt) | 2001-11-30 |
| MX9708588A (es) | 1998-09-30 |
| IN186809B (enExample) | 2001-11-10 |
| ES2157509T3 (es) | 2001-08-16 |
| ID18090A (id) | 1998-02-26 |
| CN1189393A (zh) | 1998-08-05 |
| EP0841088A3 (de) | 1998-07-22 |
| CN1100602C (zh) | 2003-02-05 |
| AR010555A1 (es) | 2000-06-28 |
| JPH10137578A (ja) | 1998-05-26 |
| ZA9710042B (en) | 1998-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |