JP7267439B2 - マイクロカプセルの調製のためのプロセス - Google Patents
マイクロカプセルの調製のためのプロセス Download PDFInfo
- Publication number
- JP7267439B2 JP7267439B2 JP2021547384A JP2021547384A JP7267439B2 JP 7267439 B2 JP7267439 B2 JP 7267439B2 JP 2021547384 A JP2021547384 A JP 2021547384A JP 2021547384 A JP2021547384 A JP 2021547384A JP 7267439 B2 JP7267439 B2 JP 7267439B2
- Authority
- JP
- Japan
- Prior art keywords
- microcapsules
- isocyanate
- methyl
- oil
- aqueous phase
- 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.)
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- 239000003094 microcapsule Substances 0.000 title claims description 146
- 238000000034 method Methods 0.000 title claims description 70
- 230000008569 process Effects 0.000 title claims description 53
- 238000002360 preparation method Methods 0.000 title description 7
- 239000002775 capsule Substances 0.000 claims description 81
- -1 cleaners Substances 0.000 claims description 61
- 239000008346 aqueous phase Substances 0.000 claims description 60
- 239000004480 active ingredient Substances 0.000 claims description 54
- 239000012948 isocyanate Substances 0.000 claims description 47
- 150000002513 isocyanates Chemical class 0.000 claims description 45
- 230000002209 hydrophobic effect Effects 0.000 claims description 36
- 239000000084 colloidal system Substances 0.000 claims description 35
- 238000004132 cross linking Methods 0.000 claims description 35
- 230000001681 protective effect Effects 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 34
- 150000001299 aldehydes Chemical class 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 23
- 230000002378 acidificating effect Effects 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000003205 fragrance Substances 0.000 claims description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000003995 emulsifying agent Substances 0.000 claims description 14
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 11
- 239000003599 detergent Substances 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 9
- 229920000881 Modified starch Polymers 0.000 claims description 8
- 229920002396 Polyurea Polymers 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 8
- 239000000796 flavoring agent Substances 0.000 claims description 8
- 235000019426 modified starch Nutrition 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229920002472 Starch Polymers 0.000 claims description 7
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002979 fabric softener Substances 0.000 claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- 235000019698 starch Nutrition 0.000 claims description 7
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 claims description 6
- 239000004368 Modified starch Substances 0.000 claims description 6
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 6
- 150000002540 isothiocyanates Chemical class 0.000 claims description 6
- 229960005337 lysine hydrochloride Drugs 0.000 claims description 6
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003623 enhancer Substances 0.000 claims description 5
- 235000019634 flavors Nutrition 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 238000007046 ethoxylation reaction Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000007764 o/w emulsion Substances 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940127557 pharmaceutical product Drugs 0.000 claims description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 4
- 235000013824 polyphenols Nutrition 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 229920002545 silicone oil Polymers 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 claims description 2
- CWRORZJYSUFYHO-UHFFFAOYSA-N (3z)-3-diazobicyclo[2.2.2]octane Chemical group C1CC2C(=[N+]=[N-])CC1CC2 CWRORZJYSUFYHO-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 2
- 229940031723 1,2-octanediol Drugs 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000077 insect repellent Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 2
- 229960003244 ornithine hydrochloride Drugs 0.000 claims description 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000004072 triols Chemical class 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 235000013373 food additive Nutrition 0.000 claims 1
- 239000002778 food additive Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 description 65
- 235000019198 oils Nutrition 0.000 description 65
- 239000002304 perfume Substances 0.000 description 62
- 239000011257 shell material Substances 0.000 description 34
- 239000011162 core material Substances 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 23
- 239000000839 emulsion Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 19
- 239000002245 particle Substances 0.000 description 19
- 238000005538 encapsulation Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000005442 diisocyanate group Chemical group 0.000 description 11
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 10
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- 238000004945 emulsification Methods 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 8
- GWCRPYGYVRXVLI-UHFFFAOYSA-N 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone Chemical compound CCC1OC(C)=C(O)C1=O GWCRPYGYVRXVLI-UHFFFAOYSA-N 0.000 description 7
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002888 zwitterionic surfactant Substances 0.000 description 7
- JIMGVOCOYZFDKB-UHFFFAOYSA-N 2-phenylethyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OCCC1=CC=CC=C1 JIMGVOCOYZFDKB-UHFFFAOYSA-N 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 6
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 6
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 6
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 5
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 5
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 229960002903 benzyl benzoate Drugs 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- SSNZFFBDIMUILS-UHFFFAOYSA-N dodec-2-enal Chemical compound CCCCCCCCCC=CC=O SSNZFFBDIMUILS-UHFFFAOYSA-N 0.000 description 5
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229920001864 tannin Polymers 0.000 description 5
- 235000018553 tannin Nutrition 0.000 description 5
- 239000001648 tannin Substances 0.000 description 5
- 235000007586 terpenes Nutrition 0.000 description 5
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 4
- DOJDQRFOTHOBEK-UHFFFAOYSA-N 1-Octen-3-yl acetate Chemical compound CCCCCC(C=C)OC(C)=O DOJDQRFOTHOBEK-UHFFFAOYSA-N 0.000 description 4
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 4
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 4
- 235000007173 Abies balsamea Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- HVJKZICIMIWFCP-UHFFFAOYSA-N Benzyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OCC1=CC=CC=C1 HVJKZICIMIWFCP-UHFFFAOYSA-N 0.000 description 4
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 4
- 244000018716 Impatiens biflora Species 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000035 biogenic effect Effects 0.000 description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 4
- 229940117916 cinnamic aldehyde Drugs 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 4
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 4
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NTOPKICPEQUPPH-UHFFFAOYSA-N isopropyl methoxy pyrazine Chemical compound COC1=NC=CN=C1C(C)C NTOPKICPEQUPPH-UHFFFAOYSA-N 0.000 description 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BSAIUMLZVGUGKX-UHFFFAOYSA-N non-2-enal Chemical compound CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 description 4
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 4
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
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- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
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- Wood Science & Technology (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
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- Toxicology (AREA)
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- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
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- Manufacturing Of Micro-Capsules (AREA)
- Polyurethanes Or Polyureas (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
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Description
・液体の扱いやすい粉体形状への変換(例えば、植物油、脂肪のコーティング);
・物質の時間制御放出(医薬品、殺虫剤及び肥料についての投与量制御、デポー効果);
・味覚、匂い及び色の補填(例えば、苦いまたはスパイスの効いた香味料);
・光、酸化、熱、酸または塩基からの保護(例えば、ビタミン類、香味料、など);
・湿気防止(例えば、吸湿性の塩またはミネラル);
・揮発性成分の喪失の遅延(例えば、芳香族化合物);
・他の混合成分との時期尚早な化学反応の防止;
・加工前または加工中のさらに良好な取り扱い(流動特性、粉塵形成);
・有害なまたは不快な物質からの職員の保護(化学物質、芳香濃縮物);または
・表面改質のよるさらに良好な溶解度/懸濁度。
・押しつぶすことまたはせん断することによってカプセルを機械的に破壊する。このメカニズムは、例えば、反応ノーカーボン紙と共に使用される。
・壁材を溶かすことによってカプセルを破壊する。このメカニズムによれば、例えば、ベーキング工程の間だけでベーキング混合物にて膨らまし剤または香味剤のような成分が放出される。
・壁材を溶解することによってカプセルを破壊する。このメカニズムは、例えば、酵素のようなカプセル封入された成分が洗浄工程の間でのみ放出されるように粉体を洗浄することにおいて使用される。
・カプセルは元のままであり、カプセルの内容物は壁材を介した拡散によって徐々に放出される。このメカニズムによれば、例えば、体内における薬物物質の緩慢で且つ均一な放出を達成することができる。
(a)2以上のイソシアネート基を有する少なくとも1つのイソシアネートまたは2以上のイソチオシアネート基を有する少なくとも1つのイソチオシアネートと、カプセル封入される疎水性有効成分とを含む内部非水性相を提供することと;
(b)少なくとも1つの保護コロイドと触媒とを含む外部水性相を提供することと;
(c)任意で安定剤及び/または乳化剤の存在下にて内部非水性相と外部水性相とを混合し、水中油型エマルションを得ることと;
(d)酸性pHで反応するアミンを加えることによって最初の架橋を行うことと;
(e)アルカリ性pHで反応するアミンを加えることによってさらなる架橋を行ってマイクロカプセルを得ることと;
(f)工程(e)で得られたマイクロカプセルを硬化することと;
任意で
(g)反応溶液からマイクロカプセルを分離し、必要に応じてマイクロカプセルを乾燥させることとを含む、またはそれらから成るイソシアネート系マイクロカプセルの調製のためのプロセスに関する。
・少なくとも1つの疎水性薬剤を含む、またはそれから成るコアと、
・酸性pHで反応するアミンによる最初の工程とアルカリ性pHで反応するアミンによるさらなる工程とにおいて保護コロイドと触媒の存在下で架橋される少なくとも2以上のイソシアネート基を有するイソシアネートを含むカプセルシェルとを含む、またはそれから成るマイクロカプセルである。
(a)2以上のイソシアネート基を有する少なくとも1つのイソシアネートまたは2以上のイソチオシアネート基を有する少なくとも1つのイソチオシアネートと、カプセル封入される疎水性有効成分とを含む内部非水性相を提供することと;
(b)少なくとも1つの保護コロイドと触媒とを含む外部水性相を提供することと;
(c)任意で安定剤及び/または乳化剤の存在下にて内部非水性相と外部水性相とを混合し、水中油型エマルションを得ることと;
(d)酸性pHで反応するアミンを加えることによって最初の架橋を行うことと;
(e)アルカリ性pHで反応するアミンを加えることによってさらなる架橋を行ってマイクロカプセルを得ることと;
(f)工程(e)で得られたマイクロカプセルを硬化することと;
任意で
(g)反応溶液からマイクロカプセルを分離し、必要に応じてマイクロカプセルを乾燥させることとを含む、またはそれらから成るイソシアネート系マイクロカプセルを調製するためのプロセスに関する。
・例えば、3-カレン;a-ピネン;ベータ-ピネン;アルファ-テルピネン;ガンマ-テルピネン;p-シメン;ビサボレン;カンフェン;カリオフィレン;セドレン;ファルネセン;リモネン;ロンギホレン;ミルセン;オシメン;バレンセン;(E,Z)-1,3,5-ウンデカトリエンのような炭化水素;
・例えば、ヘキサノール;オクタノール;3-オクタノール;2,6-ジメチルヘプタノール;2-メチルヘプタノール,2-メチルオクタノール;(E)-2-ヘキサノール;(E)-及び(Z)-3-ヘキサノール;1-オクテン-3-ol;3,4,5,6,6-ペンタメチル-3,4-ヘプテン-2-オール及び3,5,6,6-テトラメチル-4-メチレンヘプタン-2-オールの混合物;(E,Z)-2,6-ノナジエノール;3,7-ジメチル-7-メトキシオクタン-2-オール;9-デセノール;10-ウンデセノール;4-メチル-3-デセン-5-オールのような脂肪族アルコール;
・例えば、ヘキサナール;ヘプタナール;オクタナール;ノナナール;デカナール;ウンデカナール;ドデカナール;トリデカナール;2-メチルオクタナール;2-メチルノナナール;(E)-2-ヘキセナール;(Z)-4-ヘプテナール;2,6-ジメチル-5-ヘプテナール;10-ウンデセナール;(E)-4-デセナール;2-ドデセナール;2,6,10-トリメチル-5,9-ウンデカジエナール;ヘプタナールジエチルアセタール;1,1-ジメトキシ-2,2,5-トリメチル-4-ヘキセン;シトロネリルオキシアセトアルデヒドのような脂肪族アルデヒド及びそれらのアセタール;
・例えば、2-ヘプタノン;2-オクタノン;3-オクタノン;2-ノナノン;5-メチル-3-ヘプタノン;5-メチル-3-ヘプタノンオキシム;2,4,4,7-テトラメチル-6-オクテン-3-オンのような脂肪族ケトン及びそれらのオキシム;
・例えば、酢酸3-メチルチオヘキサノール;3-メチルチオヘキシル;3-メルカプトヘキサノール;酢酸3-メルカプトヘキシル;酪酸3-メルカプトヘキシル;酢酸3-アセチルチオヘキシル;1-メンテン-8-チオールのような脂肪族イオウ含有化合物;
・例えば、2-ノネン酸ニトリル;2-トリデセン酸ニトリル;2,12-トリデセン酸ニトリル;3,7-ジメチル-2,6-オクタジエン酸ニトリル;3,7-ジメチル-6-オクテン酸ニトリルのような脂肪族ニトリル;
・例えば、ギ酸(E)-及び(Z)-3-ヘキセニル;アセト酢酸エチル;酢酸イソアミル;酢酸ヘキシル;酢酸3,5,5-トリメチルヘキシル;酢酸3-メチル-2-ブテニル;酢酸(E)-2-ヘキセニル;酢酸(E)-及び(Z)-3-ヘキセニル;酢酸オクチル;酢酸3-オクチル;酢酸1-オクテン-3-イル;酪酸エチル;酪酸ブチル;酪酸イソアミル;酪酸ヘキシル;イソ酪酸(E)-及び(Z)-3-ヘキセニル;クロトン酸ヘキシル;イソ吉草酸エチル;ペンタン酸エチル2-メチル;ヘキサン酸エチル;ヘキサン酸アリル;ヘプタン酸エチル;ヘプタン酸アリル;オクタン酸エチル;(E,Z)-2,4-デカジエン酸エチル;2-オクチン酸メチル;2-ノニン酸メチル;2-イソアミルオキシ酢酸アリル;3,7-ジメチル2,6-オクタジエン酸メチルのような脂肪族カルボン酸及びそれらのエステル;
・例えば、シトロネロール;ゲラニオール;ネロール;リナロール;ラバデュロール;ネロリドール;ファルネソール;テトラヒドロリナロール;テトラヒドロゲラニオール;2,6-ジメチル-7-オクテン-2-オール;2,6-ジメチルオクタン-2-オール;2-メチル-6-メチレン-7-オクテン-2-オール;2,6-ジメチル-5,7-オクタジエン-2-オール;2,6-ジメチル-3,5-オクタジエン-2-オール;3,7-ジメチル-4,6-オクタジエン-3-オール;3,7-ジメチル-1,5,7-オクタトリエン-3-オール;2,6-ジメチル-2,5,7-オクタトリエン-I-オール及びそれらのギ酸塩、酢酸塩、プロピオン酸塩、イソ酪酸塩、酪酸塩、イソ吉草酸塩、ペンタン酸塩、ヘキサン酸塩、クロトン酸塩、チグリン酸塩、3-メチル-2-ブテン酸塩のような非環式テルペンアルコール;
・例えば、ゲラニアル;ネラール;シトロネラール;7-ヒドロキシ-3,7-ジメチルオクタナール;7-メトキシ-3,7-ジメチルオクタナール;2,6,10-トリメチル-9-ウンデセナール;ゲラニルアセトン;及びゲラニアル、ネラール、7-ヒドロキシ-3,7-ジメチルオクタナールのジメチル及びジエチルアセタールのような非環式のテルペンアルデヒド及びケトン;
・例えば、メントール;イソプレゴール;a-テルピネオール;テルピネオール-4;メンタン-8-オール;メンタン-1-オール;メンタン-7-オール;ボルネオール;イソボルネオール;酸化リナロール;ノポール;セドロール;アンブリノール;ベチベロール;グアジョール;及びそれらのギ酸塩、酢酸塩、プロピオン酸塩、イソ酪酸塩、酪酸塩、イソ吉草酸塩、ペンタン酸塩、ヘキサン酸塩、クロトン酸塩、チグリン酸塩、3-メチル-2-ブテン酸塩のような環状テルペンアルコール;
・例えば、メントン;イソメントン;8-メルカプトメンタン-3-オン;カルボン;ショウノウ;フェンコン;α-イオノン;ベータ-イオノン;α-n-メチルイオノン;ベータ-n-メチルイオノン;α-イソメチルイオノン;ベータ-イソメチルイオノン;α-イロン;s-イロン;α-ダマセノン;ベータ-ダマセノン;ガンマ-ダマセノン;d-ダマセノン;1-(2,4,4-トリメチル-2-シクロヘキセン-1-イル)-2-ブテン-1-オン;1,3,4,6,7,8a-ヘキサヒドロ-1,1,5,5-テトラメチル-2H-2,4a-メタノナフタレン-8(5H)-オン;ノートカトン;ジヒドロノートカトン;α-シネンサル;ベータ-シネンサル;アセチル化シダーウッド油(メチルセドリルケトン)のような環状テルペンアルデヒド及びケトン;
・例えば、4-tert-ブチルシクロヘキサノール;3,3,5-トリメチルシクロヘキサノール;3-イソカンフィルシクロヘキサノール;2,6,9-トリメチル-(Z2,Z5,E9)-シクロドデカトリエン-1-オール;2-イソブチル-4-メチルテトラヒドロ-2H-ピラン-4-オール;例えば、3,3,3-トリメチル-シクロヘキシルメタノール;2-メチル-4-(2,2,3-トリメチル-3-シクロペント-1-イル)ブタノール;2-メチル-4-(2,2,3-トリメチル-3-シクロペント-1-イル)-2-ブテン-1-オール;2-エチル-4-(2,2,3-トリメチル-3-シクロペント-1-イル)-2-ブテン-1-オール;3-メチル-5-(2,2,3-トリメチル-3-シクロペント-1-イル)-ペンタン-2-オール;3-メチル-5-(2,2,3-トリメチル-3-シクロペント-1-イル)-4-ペンテン-2-オール;3,3-ジメチル-5-(2,2,3-トリメチル-3-シクロペント-1-イル)-4-ペンテン-2-オール;1-(2,2,6-トリメチルシクロヘキシル)ペンタン-3-オール;1-(2,2,6-トリメチルシクロヘキシル)ヘキサン-3-オールのような環状アルコール;
・例えば、シネオール;セドリルメチルエーテル;シクロドデシルメチルエーテル;(エトキシメトキシ)シクロドデカン;a-セドレンエポキシド;3a,6,6,9a-テトラメチルドデカヒドロナフト[2,1-b]フラン;3a-エチル-6,6,9a-トリメチル-ドデカヒドロナフト[2,1-b]フラン;1,5,9-トリメチル-13-オキサビシクロ[10.1.0]トリデカ-4,8-ジエン;ローズオキシド;2-(2,4-ジメチル-3-シクロヘキセン-1-イル)-5-メチル-5-(1-メチルプロピル)-1,3-ジオキサンのような環状エーテル及び脂環族エーテル;
・例えば、4-tert-ブチルシクロヘキサノン;2,2,5-トリメチル-5-ペントylシクロペンタノン;2-ヘプチルシクロペンタノン;2-ペンチルシクロペンタノン;2-ヒドロキシ-3-メチル-2-シクロペンテン-1-オン;3-メチル-cis-2-ペンテン-1-イル-2-シクロペンテン-1-オン;3-メチル-2-ペンチル-2-シクロペンテン-1-オン;3-メチル-4-シクロペンタデセノン;3-メチル-5-シクロペンタデセノン;3-メチルシクロペンタデカノン;4-(1-エトキシビニル)-3,3,5,5-テトラメチルシクロヘキサノン;4-tert-ペンチルシクロヘキサノン;5-シクロヘキサデセン-1-オン;6,7-ジヒドロ-1,1,2,3,3-ペンタメチル-4(5H)-インダノン;9-シクロヘプタデセン-1-オン;シクロペンタデカノン;シクロヘキサデカノンのような環状ケトン;
・例えば、2,4-ジメチル-3-シクロヘキセンカルボアルデヒド;2-メチル-4-(2,2,6-トリメチル-シクロヘキセン-1-イル)-2-ブテナール;4-(4-ヒドロキシ-4-メチルペンチル)-3-シクロヘキセンカルボアルデヒド;4-(4-メチル-3-ペンテン-1-イル)-3-シクロヘキセンカルボアルデヒドのような脂環族アルデヒド;
・例えば、1-(3,3-ジメチルシクロヘキシル)-4-ペンテン-1-オン;1-(5,5-ジメチル-2-シクロヘキセン-1-イル)-4-ペンテン-1-オン;2,3,8,8-テトラメチル-1,2,3,4,5,6,7,8-オクタヒドロ-2-ナフタレニルメチルケトン;メチル-2,6,10-トリメチル-2,5,9-シクロドデカトリエニルケトン;tert-ブチル-(2,4-ジメチル-3-シクロヘキセン-1-イル)ケトンのような脂環族ケトン;
・例えば、酢酸2-tert-ブチルシクロヘキシル;酢酸4-tert-ブチルシクロヘキシル;酢酸2-tert-ペンチルシクロヘキシル;酢酸4-tert-ペンチルシクロヘキシル;酢酸デカヒドロ-2-ナフチル;酢酸3-ペンチルテトラヒドロ-2H-ピラン-4-イル;酢酸デカヒドロ-2,5,5,8a-テトラメチル-2-ナフチル;酢酸4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-または-6-インデニル;プロピオン酸4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-または-6-インデニル;イソ酪酸4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-または-6-インデニル;酢酸4,7-メタノオクタヒドロ-5-または-6-インデニルのような環状アルコールのエステル;
・例えば、プロピオン酸アリル3-シクロヘキシル;シクロヘキシルオキシ酢酸アリル;ジヒドロジャスモン酸メチル;ジャスモン酸メチル;2-ヘキシル-3-オキソシクロペンタンカルボン酸メチル;2-エチル-6,6-ジメチル-2-シクロヘキセンカルボン酸エチル;2,3,6,6-テトラメチル-2-シクロヘキセンカルボン酸エチル;2-メチル-1,3-ジオキソラン-2-酢酸エチルのような脂環族カルボン酸のエステル;
・例えば、スチレン及びジフェニルメタンのような芳香族炭化水素;
・例えば、ベンジルアルコール;1-フェニルエチルアルコール;2-フェニルエチルアルコール;3-フェニルプロパノール;2-フェニルプロパノール;2-フェノキシエタノール;2,2-ジメチル-3-フェニルプロパノール;2,2-ジメチル-3-(3-メチルフェニル)プロパノール;1,1-ジメチル-2-フェニル-エチルアルコール;1,1-ジメチル-3-フェニルプロパノール;1-エチル-1-メチル-3-フェニルプロパノール;2-メチル-5-フェニルペンタノール;3-メチル-5-フェニルペンタノール;3-フェニル-2-プロペン-1-オール;4-メトキシベンジルアルコール;1-(4-イソプロピルフェニル)エタノールのような芳香脂肪族アルコール;
・例えば、酢酸ベンジル;プロピオン酸ベンジル;イソ酪酸ベンジル;イソ吉草酸ベンジル;酢酸2-フェニルエチル;プロピオン酸2-フェニルエチル;イソ酪酸2-フェニルエチル;イソ吉草酸2-フェニルエチル;酢酸1-フェニルエチル;酢酸α-トリクロロメチルベンジル;酢酸a,a-ジメチルフェニルエチル;酪酸a,a-ジメチルフェニルエチル;酢酸シンナミル;イソ酪酸2-フェノキシエチル;酢酸4-メトキシベンジルのような芳香脂肪族アルコール及び脂肪族カルボン酸のエステル;
・例えば、2-フェニルエチルメチルエーテル;2-フェニルエチルイソアミルエーテル;2-フェニルエチル-1-エトキシエチルエーテル;フェニルアセトアルデヒドジメチルアセタール;フェニルアセトアルデヒドジエチルアセタール;ヒドラトロパアルデヒドジメチルアセタール;フェニルアセトアルデヒドグリセロールアセタール;2,4,6-トリメチル-4-フェニル-1,3-ジオキサン;4,4a,5,9b-テトラヒドロインデノ[1,2-d]-m-ジオキシン;4,4a,5,9b-テトラヒドロ-2,4-ジメチルインデノ[1,2-d]-m-ジオキシンのような芳香脂肪族エーテル;
・例えば、ベンズアルデヒド;フェニルアセトアルデヒド;3-フェニルプロパナール;ヒドラトロパアルデヒド;4-メチルベンズアルデヒド;4-メチルフェニルアセトアルデヒド;3-(4-エチルフェニル)-2,2-ジメチルプロパナール;2-メチル-3-(4-イソプロピルフェニル)プロパナール;2-メチル-3-(4-tert-ブチルフェニル)プロパナール;3-(4-tert-ブチルフェニル)プロパナール;シンナムアルデヒド;a-ブチルシンナムアルデヒド;a-アミルシンナムアルデヒド;a-ヘキシルシンナムアルデヒド;3-メチル-5-フェニルペンタナール;4-メトキシベンズアルデヒド;4-ヒドロキシ-3-メトキシベンズアルデヒド;4-ヒドロキシ-3-エトキシベンズアルデヒド;3,4-メチレンジオキシベンズアルデヒド;3,4-ジメトキシベンズアルデヒド;2-メチル-3-(4-メトキシフェニル)プロパナール;2-メチル-3-(4-メチレンジオキシフェニル)プロパナールのような芳香族及び芳香脂肪族のアルデヒド;
・例えば、アセトフェノン;4-メチルアセトフェノン;4-メトキシアセトフェノン;4-tert-ブチル-2,6-ジメチルアセトフェノン;4-フェニル-2-ブタノン;4-(4-ヒドロキシフェニル)-2-ブタノン;1-(2-ナフタレニル)エタノン;ベンゾフェノン;1,1,2,3,6-ヘキサメチル-5-インダニメチルケトン;6-tert-ブチル-1,1-ジメチル-4-インダニルメチルケトン;1-[2,3-ジヒドロ-1,1,2,6-テトラメチル-3-(1-メチルエチル)-1H-5-インデニル]エタノン;5’,6’,7’,8’-テトラヒドロ-3’,5’,5’,6’,8’,8’-ヘキサメチル-2-アセトナフトンのような芳香族及び芳香脂肪族のケトン;
・例えば、安息香酸;フェニル酢酸;安息香酸メチル;安息香酸エチル;安息香酸ヘキシル;安息香酸ベンジル;酢酸メチルフェニル;酢酸エチルフェニル;酢酸ゲラニルフェニル;酢酸フェニルエチルフェニル;桂皮酸メチル;桂皮酸エチル;桂皮酸ベンジル;桂皮酸フェニルエチル;桂皮酸シンナミル;酢酸アリルフェノキシ;サリチル酸メチル;サリチル酸イソアミル;サリチル酸ヘキシル;サリチル酸シクロヘキシル;サリチル酸cis-3-ヘキセニル;サリチル酸ベンジル;サリチル酸フェニルエチル;2,4-ジヒドロキシ-3,6-ジメチル安息香酸メチル;グリシド酸エチル3-フェニル;グリシド酸エチル3-メチル-3-フェニルのような芳香族及び芳香脂肪族のカルボン酸及びそのエステル;
・例えば、2,4,6-トリニトロ-1,3-ジメチル-5-tert-ブチルベンゼン;3,5-ジニトロ-2,6-ジメチル-4-tert-ブチルアセトフェノン;桂皮酸ニトリル;5-フェニル-3-メチル-2-ペンテン酸ニトリル;5-フェニル-3-メチルペンタン酸ニトリル;アントラニル酸メチル;アントラニル酸メチルN-メチル;メチルアントラニル酸の7-ヒドロキシ-3,7-ジメチルオクタナール、2-メチル-3-(4-tert-ブチルフェニル)プロパナールまたは2,4-ジメチル-3-シクロヘキセンカルボアルデヒドによるSchiff塩基;6-イソプロピルキノリン;6-イソブチルキノリン;6-sec-ブチルキノリン;インドール;スカトール;2-メトキシ-3-イソプロピルピラジン;2-イソブチル-3-メトキシピラジン;4-(4,8-ジメチル-3,7-ノナジエニル)-ピリジンのような窒素含有芳香族化合物;
・例えば、タラゴール;アネトール;ユーゲノール;ユーゲニルメチルエーテル;イソユーゲノール;イソユーゲニルメチルエーテル;チモール;カルバクロール;ジフェニルエーテル;ベータ-ナフチルメチルエーテル;ベータ-ナフチルエチルエーテル;ベータ-ナフチルイソブチルエーテル;1,4-ジメトキシベンゼン;酢酸ユーゲニル;2-メトキシ-4-メチルフェノール;2-エトキシ-5-(1-プロペニル)フェノール;酢酸p-クレシルフェニル;例えば、2,5-ジメチル-4-ヒドロキシ-2H-フラン-3-オン;2-エチル-4-ヒドロキシ-5-メチル-2H-フラン-3-オン;3-ヒドロキシ-2-メチル-4H-ピラン-4-オン;2-エチル-3-ヒドロキシ-4H-ピラン-4-オンのようなフェノール、フェニルエーテル及びフェニルエステル;
・例えば、1,4-オクタノリド;3-メチル-1,4-オクタノリド;1,4-ノナノリド;1,4-デカノリド;8-デセン-1,4-オリド;1,4-ウンデカノリド;1,4-ドデカノリド;1,5-デカノリド;1,5-ドデカノリド;1,15-ペンタデカノリド;cis-及びtrans-11-ペンタデセン-1,15-オールide;cis-及びtrans-12-ペンタデセン-1,15-オリド;1,16-ヘキサデカノリド;9-ヘキサデセン-1,16-オリド;10-オキサ-1,16-ヘキサデカノリド;11-オキサ-1,16-ヘキサデカノリド;12-オキサ-1,16-ヘキサデカノリド;エチレン-1,12-ドデカンジオエート;エチレン-1,13-トリデカンジオエート;クマリン;2,3-ジヒドロクマリン;オクタヒドロクマリンのようなラクトン;
と同様に上述の物質のそれぞれ立体異性体、エナンチオマー、位置異性体、ジアステレオマー、cis/trans異性体及びエピマーの1以上から選択される少なくとも1つの単独の香料または単独の香気物質、またはそれらの混合物を含む。
(i)脂肪族アルデヒド及びそのアセタール;
(ii)脂環族アルデヒド;
(iii)芳香族または芳香脂肪族のアルデヒド;
(iv)脂肪族、芳香族または芳香脂肪族のエステル;及び
(v)ラクトン
及びそれらの混合物。
・例えば、ヘキサナール;ヘプタナール;オクタナール;ノナナール;デカナール;ウンデカナール;ドデカナール;トリデカナール;2-メチルオクタナール;2-メチルノナナール;(f)-2-ヘキセナール;(Z)-4-ヘプテナール;2,6-ジメチル-5-ヘプテナール;10-ウンデセナール;(f)-4-デセナール;2-ドデセナール;2,6,10-トリメチル-5,9-ウンデカジエナール;ヘプタナールジエチルアセタール;1,1-ジメトキシ-2,2,5-トリメチル-4-ヘキセン;シトロネリルオキシアセトアルデヒドのような脂肪族アルデヒド及びそれらのアセタール;
・例えば、2,4-ジメチル-3-シクロヘキセンカルボアルデヒド;2-メチル-4-(2,2,6-トリメチル-シクロヘキセン-1-イル)-2-ブテナール;4-(4-ヒドロキシ-4-メチルペンチル)-3-シクロヘキセンカルボアルデヒド;4-(4-メチル-3-ペンテン-1-イル)-3-シクロヘキセンカルボアルデヒドのような脂環族アルデヒド;
・例えば、ベンズアルデヒド;フェニルアセトアルデヒド;3-フェニルプロパナール;ヒドラトロパアルデヒド;4-メチルベンズアルデヒド;4-メチルフェニルアセトアルデヒド;3-(4-エチルフェニル)-2,2-ジメチルプロパナール;2-メチル-3-(4-イソプロピルフェニル)プロパナール;2-メチル-3-(4-tert-ブチルフェニル)プロパナール;3-(4-tert-ブチルフェニル)プロパナール;シンナムアルデヒド;α-ブチルシンナムアルデヒド;α-アミルシンナムアルデヒド;α-ヘキシルシンナムアルデヒド;3-メチル-5-フェニルペンタナール;4-メトキシベンズアルデヒド;4-ヒドロキシ-3-メトキシベンズアルデヒド;4-ヒドロキシ-3-エトキシベンズアルデヒド;3,4-メチレンジオキシベンズアルデヒド;3,4-ジメトキシベンズアルデヒド;2-メチル-3-(4-メトキシフェニル)プロパナール;2-メチル-3-(4-メチレンジオキシフェニル)プロパナールのような芳香族及び芳香脂肪族のアルデヒド;
・例えば、ギ酸(E)-及び(Z)-3-ヘキセニル;アセト酢酸エチル;酢酸イソアミル;酢酸ヘキシル;酢酸3,5,5-トリメチルヘキシル;酢酸3-メチル-2-ブテニル;酢酸(f)-2-ヘキセニル;酢酸(E)-及び(Z)-3-ヘキセニル;酢酸オクチル;酢酸3-オクチル;酢酸1-オクテン-3-イル;酪酸エチル;酪酸ブチル;酪酸イソアミル;酪酸ヘキシル;イソ酪酸(E)-及び(Z)-3-ヘキセニル;クロトン酸ヘキシル;イソ吉草酸エチル;ペンタン酸エチル2-メチル;ヘキサン酸エチル;ヘキサン酸アリル;ヘプタン酸;ヘプタン酸アリル;オクタン酸エチル;(E,Z)-2,4-デカジエン酸エチル;2-オクチン酸メチル;2-ノニン酸メチル;2-イソアミルオキシ酢酸アリル;3,7-ジメチル2,6-オクタジエン酸メチルのような脂肪族カルボン酸のエステル;
・例えば、酢酸2-tert-ブチルシクロヘキシル;酢酸4-tert-ブチルシクロヘキシル;酢酸2-tert-ペンチルシクロヘキシル;酢酸4-tert-ペンチルシクロヘキシル;酢酸デカヒドロ-2-ナフチル;酢酸3-ペンチルテトラヒドロ-2H-ピラン-4-イル;酢酸デカヒドロ-2,5,5,8a-テトラメチル-2-ナフチル;酢酸4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-または-6-インデニル;プロピオン酸4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-または-6-インデニル;イソ酪酸4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-または-6-インデニル;酢酸4,7-メタノオクタヒドロ-5-または-6-インデニルのような環状アルコールのエステル;
・例えば、酢酸ベンジル;プロピオン酸ベンジル;イソ酪酸ベンジル;イソ吉草酸ベンジル;酢酸2-フェニルエチル;プロピオン酸2-フェニルエチル;イソ酪酸2-フェニルエチル;イソ吉草酸2-フェニルエチル;酢酸1-フェニルエチル;酢酸α-トリクロロメチルベンジル;酢酸α,α-ジメチルフェニルエチル;酪酸α,α-ジメチルフェニルエチル;酢酸シンナミル;イソ酪酸2-フェノキシエチル;酢酸4-メトキシベンジルのような芳香脂肪族アルコール及び脂肪族カルボン酸のエステル;
・例えば、プロピオン酸アリル3-シクロヘキシル;シクロヘキシルオキシ酢酸アリル;ジヒドロジャスモン酸メチル;ジャスモン酸メチル;2-ヘキシル-3-オキソシクロペンタンカルボン酸メチル;2-エチル-6,6-ジメチル-2-シクロヘキセンカルボン酸エチル;2,3,6,6-テトラメチル-2-シクロヘキセンカルボン酸エチル;2-メチル-1,3-ジオキソラン-2-酢酸エチルのような脂環族カルボン酸のエステル;
・例えば、安息香酸メチル;安息香酸エチル;安息香酸ヘキシル;安息香酸ベンジル;酢酸メチルフェニル;酢酸エチルフェニル;酢酸ゲラニルフェニル;酢酸フェニルエチルフェニル;桂皮酸メチル;桂皮酸エチル;桂皮酸ベンジル;桂皮酸フェニルエチル;桂皮酸シンナミル;酢酸アリルフェノキシ;サリチル酸メチル;サリチル酸イソアミル;サリチル酸ヘキシル;サリチル酸シクロヘキシル;サリチル酸cis-3-ヘキセニル;サリチル酸ベンジル;サリチル酸フェニルエチル;2,4-ジヒドロキシ-3,6-ジメチル安息香酸メチル;グリシド酸エチル3-フェニル;グリシド酸エチル3-メチル-3-フェニルのような芳香族及び芳香脂肪族のカルボン酸エステル;
の1以上から選択される。
O=C=N-R-N=C=O + -(CH2-CH(OH)-)n- → -(R-O-CO-NH-R-NH-CO-O-)n
本発明に係るイソシアネート系マイクロカプセルの製造について、外部水性相が溶解されたまたは分散されたさらなる保護コロイド及び/または安定剤及び/または乳化助剤を任意で含有していれば、それは有利であることができる。そのような薬剤は、例えば、水性相の総重量を基にして0.05~5重量%、好ましくは0.1~4重量%の量で加えることができる。
・8~22の炭素原子を含有する直鎖脂肪アルコール、12~22の炭素原子を含有する脂肪酸、アルキル基にて8~15の炭素原子を含有するアルキルフェノール及びアルキルラジカルにて8~22の炭素原子を含有するアルキルアミンに対する2~30モルのエチレンオキシド及び/または0~5モルのプロピレンオキシドの付加生成物;
・アルキル/アルケニルラジカルにて8~22の炭素原子を持つアルキルオリゴグリコシド及び/またはアルケニルオリゴグリコシド及びそれらのエトキシル化類似体;
・ヒマシ油及び/または硬化ヒマシ油に対する1~15モルのエチレンオキシドの付加生成物;
・ヒマシ油及び/または硬化ヒマシ油に対する15~60モルのエチレンオキシドの付加生成物;
・12~22の炭素原子を含有する不飽和直鎖または飽和分岐鎖の脂肪酸及び/または3~18の炭素原子を含有するヒドロキシカルボン酸によるグリセロール及び/またはソルビタンの部分エステル、及び1~30モルのエチレンオキシドによるそれらの付加体;
・12~22の炭素原子を含有する飽和及び/または不飽和の直鎖または分岐鎖の脂肪酸及び/または3~18の炭素原子を含有するヒドロキシカルボン酸によるポリグリセロール(2~8の平均自己縮合度)、ポリエチレングリコール(分子量400~5000)、トリメチロールプロパン、ペンタエリスリトール、糖アルコール(例えば、ソルビトール)、アルキルグルコシド(例えば、メチルグルコシド、ブチルグルコシド、ラウリルグルコシド)及びポリグルコシド(例えば、セルロース)の部分エステル、と同様に1~30モルのエチレンオキシドによるそれらの付加体、好ましくはCremophor(登録商標);
・ペンタエリスリトール、脂肪酸、クエン酸及び脂肪アルコールの混合エステル及び/または6~22の炭素原子を持つ脂肪酸、メチルグルコース及びポリオール、好ましくはグリセロールまたはポリグリセロールの混合エステル;
・リン酸モノアルキル、リン酸ジアルキル及びリン酸トリアルキル、と同様にリン酸モノPEG-アルキル、ジPEG-アルキル及びトリPEG-アルキル、及びそれらの塩;
・羊毛脂アルコール;
・ポリシロキサン-ポリアルキル-ポリエーテルコポリマーまたは対応する誘導体;ブロックコポリマー、例えば、ポリエチレングリコール-30ジポリヒドロキシステアレート;ポリマー乳化剤、例えば、GoodrichのPemulen等級(TR-1、TR-2)またはCognisのCosmedia(登録商標)SP;
・ポリアルキレングリコール及び炭酸グリセロール
の少なくとも1つに由来する非イオン性界面活性剤が挙げられる。
・d(0.1)値:カプセルの10%はこの値より小さい;
・d(0.5)値:カプセルの50%はこの値より大きく、カプセルの50%は小さい。
・d(0.9)値:カプセルの10%はこの値より大きい。
・少なくとも1つの疎水性薬剤を含むまたはそれから成るコア;と
・最初の工程にて保護コロイドと触媒の存在下、酸性pHで反応するアミンによって及びさらなる工程にてアルカリ性pHで反応するアミンによって架橋される2以上のイソシアネート基を有するイソシアネートを含むカプセルシェルとを含む、またはそれらから成るマイクロカプセルである。
触媒(DABCO)、20~30℃での最初の架橋剤(塩酸リジン)及び35~50℃での別の架橋剤(炭酸グアニジニウム)の有無にて本発明の方法に従って調製したマイクロカプセルの安定性データ。ポリビニルアルコールを保護コロイドとして使用した。
さまざまな保護コロイドとともに本発明の方法によって調製したマイクロカプセルの安定性データ:5.0のpHでの塩酸リジンによる架橋;カプセル封入された油:カレンデルタ-3nat、カリオフィレンnat.rect.、フェランドレンI、ピネネアルファlaevo nat.、テルピネンガンマ、ベルドラシン。
香油4の実施例にてシェルの縮小を実施した。内部非水性相でのモノマー(イソシアネート)の含量を減らした。
従来技術のカプセル封入技術によって及び本発明に係る方法によって製造されたマイクロカプセルの安定性の比較
カプセルシェルの多分子層の形成
本発明に係るマイクロカプセルの官能評価
本発明に係るシェルを減らしたカプセル:10日間50℃、59%香油
Claims (14)
- イソシアネート系マイクロカプセルを調製するプロセスであって、以下の工程:
(a)2以上のイソシアネート基を有する少なくとも1つのイソシアネートまたは2以上のイソチオシアネート基を有する少なくとも1つのイソチオシアネートと、カプセル封入される疎水性薬剤とを含む内部非水性相を提供することと;
(b)少なくとも1つの保護コロイドと触媒とを含む外部水性相を提供することと;
(c)任意で安定剤及び/または乳化剤の存在下にて前記内部非水性相と前記外部水性相とを混合し、水中油型エマルションを得ることと;
(d)酸性アミノ酸の塩酸塩から成る群から選択される、酸性pHで反応するアミンの添加によって最初に架橋を行うことと;
(e)ジアミン、トリアミン及びポリアミン及び炭酸グアニジニウムから成る群から選択される、アルカリ性pHで反応するアミンの添加によってさらなる架橋を行ってマイクロカプセルを得ることと;
(f)工程(e)で得られた前記マイクロカプセルを硬化することと;
任意で
(g)前記反応溶液から前記マイクロカプセルを分離し、必要に応じて前記マイクロカプセルを乾燥させることと、を含む、前記プロセス。 - 2以上のイソシアネート基を有する前記イソシアネートまたは2以上のイソチオシアネート基を有する前記イソチオシアネートが、脂肪族、脂環族、ヒドロ芳香族、芳香族、または複素環のポリイソシアネートまたはポリイソチオシアネート、それらの置換生成物及び前述の化合物の混合物から成る群から選択される、請求項1に記載のプロセス。
- カプセル封入される前記少なくとも1つの疎水性有効成分が、香料、芳香物質、殺生物剤、殺昆虫剤;防虫剤、食品添加物、化粧品有効成分、医薬品有効成分、農薬、染料、発光染料、光学的光沢剤、溶媒、蝋状物質、シリコーン油、潤滑剤の群由来の物質;と同様に前記有効成分の混合物から成る群から選択される、先行請求項1または2のいずれか1項に記載のプロセス。
- カプセル封入される前記少なくとも1つの疎水性有効成分が、アルデヒド、カルボン酸、またはエステルの官能性を有する香料または香味剤から成る群から選択される、先行請求項1~3のいずれか1項に記載のプロセス。
- 前記保護コロイドが、ジオール、エタンジオール、1,2-プロパンジオール、1,3-プロパンジオール、1,2-ブタンジオール、異性体ブタンジオール、1,2-ペンタンジオール、1,2-ヘキサンジオール、1,2-オクタンジオール、1,2-デカンジオール、1,2-ドデカンジオール、ポリオール、トリオール、グリセロール、と同様にそのエトキシル化及びプロポキシル化の生成物、トリメチロールプロパン及びそのエトキシル化及びプロポキシル化の生成物、ポリビニルアルコール(PVOH)及びその誘導体、アンモニウム-またはスルホネートで官能化されたポリビニルアルコール、ポリフェノール、1,3,5-トリヒドロキシベンゼン、デンプン、化学的に、機械的に及び/または酵素的に修飾したデンプン、カルボキシメチルセルロース、ポリビニルピロリドン、及び前記化合物の混合物から成る群から選択される、先行請求項1~4のいずれか1項に記載のプロセス。
- 前記保護コロイドがデンプンとの組み合わせで使用される、先行請求項1~5のいずれか1項に記載のプロセス。
- 前記触媒がジアゾビシクロ[2.2.2]オクタン(DABCO)である、先行請求項1~6のいずれか1項に記載のプロセス。
- 酸性pHにて反応する前記アミンによる前記最初の架橋が2~7のpH及び任意で20℃~30℃の温度にて生じる、先行請求項1~7のいずれか1項に記載のプロセス。
- 前記酸性で反応するアミンが塩酸リジン及び塩酸オルニチンから成る群から選択される、先行請求項1~8のいずれか1項に記載のプロセス。
- 前記アルカリ性で反応するアミンによる前記さらなる架橋が7~14のpH及び任意で35℃~50℃の温度で生じる、先行請求項1~9のいずれか1項に記載のプロセス。
- 工程(f)における前記マイクロカプセルの前記硬化が55℃~70℃までの温度で実施される、先行請求項1~10のいずれか1項に記載のプロセス。
- イソシアネート系マイクロカプセルまたはそのマイクロカプセルを含む懸濁液であって、
・少なくとも1つの疎水性薬剤を含むコアと;
・保護コロイドと触媒の存在下、酸性アミノ酸の塩酸塩から成る群から選択される、酸性pHで反応するアミンによる最初の工程と、ジアミン、トリアミン及びポリアミン及び炭酸グアニジニウムから成る群から選択される、アルカリ性pHで反応するアミンによるさらなる工程とにおいて架橋された2以上のイソシアネート基を有するイソシアネートを含んで成るカプセルシェルと、を含むまたはそれらから成る、前記イソシアネート系マイクロカプセル。 - 前記カプセルシェルがポリウレタンの第1の層とポリウレアの第2の層とを含む、またはそれらから成る、請求項12に記載のイソシアネート系マイクロカプセルまたはそのマイクロカプセルを含む懸濁液。
- 洗剤、布地柔軟剤、洗浄剤、液状形態または固形状形態の香りブースター、液状形態または固形状形態の香料増強剤、化粧品、パーソナルケア製品、農業製品または医薬製品の製造のための、請求項12または13に記載のマイクロカプセルまたは請求項12または13に記載のマイクロカプセルを含む懸濁液の使用。
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