JP6153944B2 - マイクロカプセル - Google Patents
マイクロカプセル Download PDFInfo
- Publication number
- JP6153944B2 JP6153944B2 JP2014550448A JP2014550448A JP6153944B2 JP 6153944 B2 JP6153944 B2 JP 6153944B2 JP 2014550448 A JP2014550448 A JP 2014550448A JP 2014550448 A JP2014550448 A JP 2014550448A JP 6153944 B2 JP6153944 B2 JP 6153944B2
- Authority
- JP
- Japan
- Prior art keywords
- formaldehyde
- substituted
- urea
- composition
- weight
- 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.)
- Active
Links
- 239000003094 microcapsule Substances 0.000 title claims description 61
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 254
- 239000000203 mixture Substances 0.000 claims description 91
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 62
- 239000004202 carbamide Substances 0.000 claims description 34
- 239000007795 chemical reaction product Substances 0.000 claims description 32
- 229920000877 Melamine resin Polymers 0.000 claims description 29
- 239000006185 dispersion Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 26
- 239000002516 radical scavenger Substances 0.000 claims description 25
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 25
- 229920003180 amino resin Polymers 0.000 claims description 24
- 239000000376 reactant Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 12
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 10
- 229920000768 polyamine Polymers 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 7
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001694 spray drying Methods 0.000 claims description 6
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 4
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical class O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 6
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- OKDWFIMHZAXBAG-UHFFFAOYSA-N 1-amino-2-ethylpropane-1,3-diol Chemical compound CCC(CO)C(N)O OKDWFIMHZAXBAG-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000011162 core material Substances 0.000 description 23
- -1 urea compound Chemical class 0.000 description 22
- 239000008199 coating composition Substances 0.000 description 20
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000002245 particle Substances 0.000 description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000013535 sea water Substances 0.000 description 12
- 239000011257 shell material Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000012445 acidic reagent Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 description 4
- 239000003139 biocide Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 0 *C(C(*)(*)O)N* Chemical compound *C(C(*)(*)O)N* 0.000 description 2
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 2
- 101150035093 AMPD gene Proteins 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000003373 anti-fouling effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000007771 core particle Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000012066 reaction slurry Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003878 thermal aging Methods 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- IYNGLSRZLOHZJA-UHFFFAOYSA-N 1,4,7-triazabicyclo[5.2.2]undecane Chemical compound C1CN2CCN1CCNCC2 IYNGLSRZLOHZJA-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000700670 Bryozoa Species 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 241000238586 Cirripedia Species 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 241000243820 Polychaeta Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000243142 Porifera Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012429 release testing Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- 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
-
- 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
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
-
- 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
- B01J13/20—After-treatment of capsule walls, e.g. hardening
-
- 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
- B01J13/20—After-treatment of capsule walls, e.g. hardening
- B01J13/206—Hardening; drying
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Paints Or Removers (AREA)
Description
マイクロカプセルを、米国特許第6486099号明細書に記載の通りに調製した。殺生物剤である活性4,5−ジクロロ−2−n−オクチル−4−イソチアゾリン−3−オン(DCOIT)(235g)を、ケトル準備直前に融解させた。水を、機械的混合装置、温度制御装置及び入口/出口ポンピングラインを備えたケトルに加えた。ケトルを50℃まで加熱した。次に、33.8gのU−Ramin(商標)P−1500カチオンウレア−ホルムアルデヒドプレポリマー(溶液の重量を基準として濃度40重量%)水溶液(Mitsui Kagaku K.K.製)をケトルに加え、続いてトリエタノールアミンを添加し、クエン酸でpHを調節した。速やかに、融解したDCOIT及びナトリウムドデシルベンゼンスルホネートの水溶液をケトルに撹拌しながら加えた。粗大エマルションを、Silversonインラインミキサ又はIKA Magic Lab(商標)ミキサ(IKA製)でのポンプ輸送により乳化させた。
マイクロカプセルのウェットケークを、穏やかに撹拌しながら30分間にわたって水に再分散させた。ターゲットスラリー固形分は20%であった。得られたスラリーをBuchi(商標)スプレードライヤー(Buchi製)にポンプ輸送した。入口温度を155℃に設定し、出口温度を77℃に設定した。真空圧を20mmHgに設定した。霧化用ガスを600L/時間に設定した。乾燥粉末をサイクロンで捕集した。
0.6グラムのカプセルを、100mLオートクレーブボトルに入れた。50グラムの40%MIBK/60%キシレン(重量/重量で調製)をボトルに加えた。1時間後、試料を取り出し、「0日目」とラベルをつけた。次にボトルを50℃に設定した炉に入れた。試料を、1、3又は4、7、14、21、28、56及び84日目に取り出した。各試料について、20.0マイクロリットルの溶媒層をボトルからピペットで取り出し、0.2マイクロメートルフィルタを備えた3mLシリンジに入れた。次に、980mLのアセトニトリル(ACN)をピペットでこの3mLシリンジに加え、混合物をオートサンプラーバイアルに濾過した。各オートサンプラーバイアル中のDCOIT含有量を、HPLCで測定した。
放出%DCOIT=100%x50(希釈係数)X(バイアル中のDCOITのppm)/(DCOIT充填レベル)
DCOIT充填レベル=マイクロカプセルからの全DCOITx(カプセル重量)/(溶媒重量)
4.00mLの6g/L硫酸銅5水和物溶液を4リットルのRicca(商標)海水(重金属非含有ASTM D1141人工海水。Ricca chemicalsから入手可能)に添加することで合成海水を調製した。1986.6グラムのこの溶液を、13.4グラムのDowfax(商標)2A1界面活性剤(Dow Chemical Co.製)と混合し、5分間にわたって混合し、次に0.2マイクロメートルフィルタで濾過した。
REL=100%x(オートサンプラーバイアル中のDCOITのppm)/(有効成分の充填レベル)
有効成分の充填レベル=(マイクロカプセルからの全AI)x(カプセルの重量)/(海水の重量)
SWRR=(28日目のREL−1日目のREL)/27
10gのマイクロカプセルを閉鎖バイアルに入れ、このバイアルを次に80℃の炉に1日入れた。SWRRを実施例3に記載の通りに測定した。熱エージング後のSWRRの保持性(RET)を、以下の式で計算する。
RET=100*(熱エージング処理カプセルのSWRR/無処理カプセルのSWRR)
PSDを、2000μPモジュールを備えたMalvern Mastersizer(商標)2000機器(Malvern製)で測定した。噴霧乾燥させた粉末をキシレン中に分散させ、測定を、検出セルにおいてキシレンで更に希釈して行った。粒径d(0.5)及びd(0.9)を報告した。
添加剤を添加したマイクロカプセルの噴霧乾燥手順
各添加剤を、最終粉末重量を基準として、表に記載の量で水に溶解させた。マイクロカプセルウェットケークを撹拌により、添加溶液に30分間にわたって再分散させた。得られるスラリーにおけるマイクロカプセルウェットケークの量は、スラリーの重量を基準として20重量%であった。
Claims (8)
- マイクロカプセルを含み、
前記マイクロカプセルがコアと外方シェルとを含み、
前記コアが、15℃より高い融点を有する1種以上の4−イソチアゾリン−3−オンの水不溶性誘導体を含み、
前記外方シェルが、1種以上のポリアミン及びホルムアルデヒドを含む反応物の反応生成物である1種以上のアミノ樹脂を含み、
1種以上のホルムアルデヒド捕捉剤、前記アミノ樹脂とホルムアルデヒド捕捉剤との1種以上の反応生成物又はこれらの混合物を更に含み、
前記アミノ樹脂とホルムアルデヒド捕捉剤との反応生成物の前記ホルムアルデヒド捕捉剤+ホルムアルデヒド反応物当量の合計重量が、組成物の重量を基準として10%以上であり、
前記ホルムアルデヒド捕捉剤が、構造I、II、III又はIV:
組成物。 - 前記ホルムアルデヒド捕捉剤が、ウレア、エチレンウレア、ジヒドロキシエチレンウレア(DHEU)、2−アミノ−2−メチルプロパノール(AMP)、2−アミノ−2−メチル−1,3−プロパンジオール(AMPD)、2−アミノ−2−エチル−1,3−プロパンジオール(AEPD)、トリス(ヒドロキシメチル)アミノメタン(TRIS)、メラミン、レゾルシノール、N−メチロールアクリルアミド、ジエタノールアミン及びこれらの混合物から成る群から選択される1種以上の化合物を含む、請求項1に記載の組成物。
- 前記ホルムアルデヒド捕捉剤が、ウレア、エチレンウレア、トリス(ヒドロキシメチル)アミノメタン(TRIS)、メラミン、レゾルシノール、N−メチロールアクリルアミド、ジエタノールアミン及びこれらの混合物から成る群から選択される1種以上の化合物を含む、請求項1に記載の組成物。
- 前記ホルムアルデヒド捕捉剤が、ウレア、エチレンウレア、トリス(ヒドロキシメチル)アミノメタン(TRIS)及びこれらの混合物から成る群から選択される1種以上の化合物を含む、請求項1に記載の組成物。
- 前記ポリアミンが、ウレア及びメラミンを含む、請求項1に記載の組成物。
- マイクロカプセルを形成し、次に前記マイクロカプセルと1種以上のホルムアルデヒド捕捉剤との混合物を調製するステップを含み、
前記マイクロカプセルがコアと外方シェルとを含み、
前記コアが、15℃より高い融点を有する1種以上の4−イソチアゾリン−3−オンの水不溶性誘導体を含み、
前記外方シェルが、1種以上のポリアミン及びホルムアルデヒドを含む反応物の反応生
成物である1種以上のアミノ樹脂を含み、
前記アミノ樹脂とホルムアルデヒド捕捉剤との反応生成物の前記ホルムアルデヒド捕捉剤+ホルムアルデヒド反応物当量の合計重量が、組成物の重量を基準として10%以上であり、
前記ホルムアルデヒド捕捉剤が、構造I、II、III又はIV:
マイクロカプセルを含む組成物の製造方法。 - (i)前記マイクロカプセルの水中分散物を調製するステップと、
(ii)前記分散物に前記ホルムアルデヒド捕捉剤を添加するステップと、
(iii)ステップ(i)及び(ii)に続いて、前記マイクロカプセルの前記分散物
を乾燥させるステップを含む、
請求項6に記載の方法。 - 前記乾燥を、噴霧乾燥によって行う、請求項7に記載の方法。
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US201161580447P | 2011-12-27 | 2011-12-27 | |
US61/580,447 | 2011-12-27 | ||
PCT/US2012/071738 WO2013101887A2 (en) | 2011-12-27 | 2012-12-27 | Microcapsules |
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EP (1) | EP2775832A2 (ja) |
JP (1) | JP6153944B2 (ja) |
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JP6433060B2 (ja) * | 2013-11-26 | 2018-12-05 | ダウ グローバル テクノロジーズ エルエルシー | 脂肪族または脂環式ジカルボキシアルデヒドおよびレゾルシノールの水性バインダー組成物 |
KR101726372B1 (ko) | 2015-05-27 | 2017-04-13 | 한국과학기술연구원 | 자가치유 마이크로캡슐, 이를 포함하는 자가치유 시스템 및 이의 제조 방법 |
WO2016201615A1 (en) * | 2015-06-16 | 2016-12-22 | Air Products And Chemicals, Inc. | Aldehyde scavengers for polyurethane foams |
US10696777B2 (en) | 2015-06-16 | 2020-06-30 | Evonik Operations Gmbh | Aldehyde scavengers mixtures for polyurethane foams |
CN105032178A (zh) * | 2015-07-03 | 2015-11-11 | 吴永顺 | 纳米本草甲醛有机除味剂 |
WO2017095335A1 (en) * | 2015-11-30 | 2017-06-08 | Aquafil S.P.A. | Microencapsulated biocides, coating compositions with microencapsulated biocides and use of coating compositions for fishing nets |
WO2019133483A1 (en) * | 2017-12-28 | 2019-07-04 | Dow Global Technologies Llc | Stabilization of dcoit in aqueous systems |
KR102230501B1 (ko) * | 2019-11-04 | 2021-03-22 | 한국생산기술연구원 | 마이크로캡슐화된 무기계 난연 첨가제를 포함하는 난연 섬유 및 그의 제조방법 |
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JPS58124705A (ja) * | 1982-01-18 | 1983-07-25 | Kureha Chem Ind Co Ltd | マイクロカプセル化農薬及びその製造方法 |
JPS58139738A (ja) * | 1982-02-13 | 1983-08-19 | Mitsubishi Paper Mills Ltd | 微小カプセル |
US4610927A (en) * | 1983-09-14 | 1986-09-09 | Kureha Kagaku Kogyo Kabushiki Kaisha | Microcapsules containing a hydrophobic, volatile core substance and their production |
ES2017536T5 (es) * | 1987-12-21 | 1995-08-01 | Koehler August Papierfab | Procedimiento para la fabricacion de microcapsulas, microcapsulas obtenidas y su utilizacion. |
JPH0952805A (ja) * | 1995-08-10 | 1997-02-25 | Agro Kanesho Co Ltd | 2,6−ジクロロベンゾニトリルマイクロカプセル化除草製剤 |
DE10000621A1 (de) * | 2000-01-10 | 2001-07-12 | Basf Ag | Niedrigviskose, formaldehydreduzierte Dispersionen von Mikrokapseln aus Melamin-Formaldehyd-Harzen |
EP1118382B1 (en) | 2000-01-13 | 2003-04-02 | Kureha Kagaku Kogyo Kabushiki Kaisha | Microcapsule and process for production thereof |
CN101137288B (zh) * | 2004-09-14 | 2011-09-28 | 微技术实验室公司 | 微胶囊化的杀生物剂和防污剂 |
US20070138674A1 (en) * | 2005-12-15 | 2007-06-21 | Theodore James Anastasiou | Encapsulated active material with reduced formaldehyde potential |
US20070138671A1 (en) * | 2005-12-15 | 2007-06-21 | Anastasiou Theodore J | Encapsulated active material with reduced formaldehyde potential |
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CN104010498B (zh) | 2016-09-14 |
JP2015508399A (ja) | 2015-03-19 |
KR102094217B1 (ko) | 2020-03-27 |
WO2013101887A2 (en) | 2013-07-04 |
CL2014001601A1 (es) | 2014-11-14 |
EP2775832A2 (en) | 2014-09-17 |
US20140348937A1 (en) | 2014-11-27 |
CN104010498A (zh) | 2014-08-27 |
BR112014014285A2 (pt) | 2017-06-13 |
WO2013101887A3 (en) | 2013-08-22 |
BR112014014285B1 (pt) | 2020-05-05 |
US9924720B2 (en) | 2018-03-27 |
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