JP2018533464A - カプセル化 - Google Patents
カプセル化 Download PDFInfo
- Publication number
- JP2018533464A JP2018533464A JP2018512189A JP2018512189A JP2018533464A JP 2018533464 A JP2018533464 A JP 2018533464A JP 2018512189 A JP2018512189 A JP 2018512189A JP 2018512189 A JP2018512189 A JP 2018512189A JP 2018533464 A JP2018533464 A JP 2018533464A
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- meth
- water
- amine
- 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.)
- Granted
Links
- 238000005538 encapsulation Methods 0.000 title description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 152
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 122
- 239000012071 phase Substances 0.000 claims abstract description 101
- 239000003094 microcapsule Substances 0.000 claims abstract description 91
- 239000008346 aqueous phase Substances 0.000 claims abstract description 81
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 150000001412 amines Chemical class 0.000 claims abstract description 45
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 44
- 239000012948 isocyanate Substances 0.000 claims abstract description 41
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 38
- 239000003999 initiator Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 239000000839 emulsion Substances 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 22
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 11
- 239000002245 particle Substances 0.000 claims abstract description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 9
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims description 63
- 239000011162 core material Substances 0.000 claims description 55
- -1 hydroxyl ethyl Chemical group 0.000 claims description 47
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 25
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 18
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 18
- 229920002396 Polyurea Polymers 0.000 claims description 15
- 239000004971 Cross linker Substances 0.000 claims description 13
- 239000004814 polyurethane Substances 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 239000003205 fragrance Substances 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 4
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 4
- LLTAGRBKLBDOIZ-UHFFFAOYSA-N 3-(tert-butylamino)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCNC(C)(C)C LLTAGRBKLBDOIZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002826 coolant Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002304 perfume Substances 0.000 claims description 3
- QKYFBXHRNXDPRD-UHFFFAOYSA-N 2-(2-methylbutan-2-ylamino)ethyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCNC(C)(C)CC QKYFBXHRNXDPRD-UHFFFAOYSA-N 0.000 claims description 2
- XGBKJUZKXFOBSP-UHFFFAOYSA-N 2-(2-methylpentan-2-ylamino)ethyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCNC(C)(C)CCC XGBKJUZKXFOBSP-UHFFFAOYSA-N 0.000 claims description 2
- NMGPHUOPSWFUEB-UHFFFAOYSA-N 2-(butylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCNCCOC(=O)C(C)=C NMGPHUOPSWFUEB-UHFFFAOYSA-N 0.000 claims description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 2
- SVYHMICYJHWXIN-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethyl 2-methylprop-2-enoate Chemical compound CC(C)N(C(C)C)CCOC(=O)C(C)=C SVYHMICYJHWXIN-UHFFFAOYSA-N 0.000 claims description 2
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 claims description 2
- PCUPXNDEQDWEMM-UHFFFAOYSA-N 3-(diethylamino)propyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCCOC(=O)C(C)=C PCUPXNDEQDWEMM-UHFFFAOYSA-N 0.000 claims description 2
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 230000000975 bioactive effect Effects 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 28
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 238000002156 mixing Methods 0.000 description 49
- 239000003921 oil Substances 0.000 description 44
- 235000019198 oils Nutrition 0.000 description 44
- 238000003801 milling Methods 0.000 description 29
- 230000003134 recirculating effect Effects 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 27
- 125000000524 functional group Chemical group 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000002775 capsule Substances 0.000 description 23
- 229910000831 Steel Inorganic materials 0.000 description 22
- 239000010959 steel Substances 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 21
- 229920002554 vinyl polymer Polymers 0.000 description 16
- 229920006318 anionic polymer Polymers 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 11
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 229920000193 polymethacrylate Polymers 0.000 description 9
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 229920000058 polyacrylate Polymers 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- 239000002318 adhesion promoter Substances 0.000 description 5
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012782 phase change material Substances 0.000 description 5
- 238000012695 Interfacial polymerization Methods 0.000 description 4
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920003180 amino resin Polymers 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920000083 poly(allylamine) Polymers 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002600 sunflower oil Substances 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 235000019501 Lemon oil Nutrition 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- KXVGTQFNYXBBHD-UHFFFAOYSA-N ethenyl acetate;pyrrolidin-2-one Chemical compound CC(=O)OC=C.O=C1CCCN1 KXVGTQFNYXBBHD-UHFFFAOYSA-N 0.000 description 2
- FYTNRXSQGDWQGN-UHFFFAOYSA-N ethenyl prop-2-enoate;pyrrolidin-2-one Chemical compound O=C1CCCN1.C=COC(=O)C=C FYTNRXSQGDWQGN-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 2
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 2
- QRJPIVHLFCLJMK-UHFFFAOYSA-N ethyl prop-2-enoate;pyrrolidin-2-one Chemical compound O=C1CCCN1.CCOC(=O)C=C QRJPIVHLFCLJMK-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 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 2
- HANVTCGOAROXMV-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine;urea Chemical compound O=C.NC(N)=O.NC1=NC(N)=NC(N)=N1 HANVTCGOAROXMV-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- BJQWYEJQWHSSCJ-UHFFFAOYSA-N heptacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC BJQWYEJQWHSSCJ-UHFFFAOYSA-N 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
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Abstract
有益剤デリバリー粒子の改良された製造方法およびその方法によって製造される改良されたマイクロカプセルを開示する。本発明の方法は、水相1、水相2および水相3からなる第1の組成物を供する工程を含む。水相1は水と開始剤とを含み、水相2は水と、水溶性または水分散性アミン(メタ)アクリレートまたはヒドロキシル(メタ)アクリレートと、多官能性(メタ)アクリレートとを含む。水相3は、水とカルボキシアルキル(メタ)アクリレートと、塩基または4級アンモニウムアクリレートとを含む。最初の2つの水相が混ぜ合わされ、ヒドロキシまたはアミン(メタ)アクリレートおよび多官能性(メタ)アクリレートを予備反応させ、多官能性ヒドロキシル−アミン(メタ)アクリレートプレポリマーを形成する。このプレポリマーは、水相3と混ぜ合わされ、高せん断撹拌下で第2組成物を第1組成物内に乳化することによってエマルションが形成され、第2組成物は、イソシアネートおよび有益剤からなる芯材を含む油相を含み、これによりを有益剤からなる芯材を囲む壁を形成する。
Description
本明細書で使用する用語「(メタ)アクリレート」または「(メタ)アクリル」は、特定のモノマー、オリゴマーおよび/またはプレポリマーのアクリレートおよぼメタクリレートの両方の型を意味するもの理解されるべきである(例えば、「アリル(メタ)アクリレート」はアリルメタクリレートとアリルアクリレートの両方を表し、同様に(メタ)アクリル酸のアルキルエステルと言った場合、アクリル酸のアルキルエステルとメタクリル酸のアルキルエステルの両方があり得ることを表し、同様にポリ(メタ)アクリレートはポルアクリレートとポ(メタ)アクリレートの両方があり得ることを表す)。各アルキル部分は、特に明記しない限りC1〜C8またはC1〜C24である。ポリ(メタ)アクリレート材料は、幅広い範囲の高分子材料を包含することを意図したものであり、例えば、ポリ(メタ)アクリル酸ポリエステル、ウレタンおよびポリウレタンポリ(メタ)アクリレート(特にヒドロキシアルキル(メタ)アクリレートとウレタンポリイソシアネートまたはウレタンポリイソシアネートとの反応によって調製されるもの)、メチルシアノアクリレート、エチルシアノアクリレート、ジエチレングリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、アリル(メタ)アクリレート、グリシジル(メタ)アクリレート、(メタ)アクリレート官能性シリコーン、ジ−、トリ−およびテトラエチレングリコールジ(メタ)アクリレート、ジプロピレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、ジ(ペンタメチレングリコール)ジ(メタ)アクリレート、エチレンジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、エトキシ化ビスフェノールAジ(メタ)アクリレート、ビスフェノールAジ(メタ)アクリレート、ジグリセロールジ(メタ)アクリレート、テトラエチレングリコールジクロロアクリレート、1,3−ブタンジオールジ(メタ)アクリレート、ネオペンチルジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレートおよびジプロピレングリコールジ(メタ)アクリレートおよび種々の多官能性(メタ)アクリレートおよび多官能性アミン(メタ)アクリレート。単官能性アクリレート、即ちアクリレート基を1つだけ含むものも使用すると有利である。通常の モノアクリレートとしては、2−エチルヘキシル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、シアノエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、p−ジメチルアミノエチル(メタ)アクリレート、ラウリル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、クロロベンジル(メタ)アクリレート、アミノアルキル(メタ)アクリレート、種々のアルキル(メタ)アクリレートおよびグリシジル(メタ)アクリレートが挙げられる。当然のことながら(メタ)アクリレートまたはその誘導体の混合物だけでなく1つ以上の(メタ)アクリレートモノマー、オリゴマーおよび/またはプレポリマーまたはその誘導体とアクリロニトリル類およびメタアクリロニトリル類などの他の共重合性モノマーとを混合したものも同様に使用してもよい。
前記水相1は水と開始剤を含み、
前記水相2は水、ヒドロキシアルキル(メタ)アクリレートおよび多官能性(メタ)アクリレートを含み、
前記水相3は水とカルボキシ(メタ)アクリレートと塩基を含む。
ポリマー調製工程:水相1用に0.5グラムの水溶性開始剤(V50)をジャケット付きスチールリアクター内の40℃の水200グラムに1000rpmで混合し、100cc/分で窒素雰囲気を生成しながら加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。2.5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR415)および10グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちTBAEMA)を含む150グラムの水相2を加え、混合を1500rpmに上昇させて行う。混ぜ合わせた水相は60℃で60分間混合され、その後12.5グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(CD9055SR415)を含む150グラムの水相3を加え、その混ぜ合わせた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間その温度に保持し、完全なポリマーを形成する。
ポリマー調製工程:水相1用に0.825グラムの水溶性開始剤(V50)を1000rpmで混合し、100cc/分で窒素雰囲気を生成しながらジャケット付きスチールリアクター内の40℃の水200グラムに加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。2.5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR415)および10グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちヒドロキシエチルメタクリレート(HEMA))を含む150グラムの水相2を加え、混合速度を1500rpmに上げる。混ぜ合わせた水相を60℃で60分間混合し、その後15グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(CD9055SR415)を含む150グラムの水相3を加え、混ぜ合わせた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間95℃に保持し、完全なポリマーを形成する。
ポリマー調製工程:水相1用に0.5グラムの水溶性開始剤(V50)を1000rpmで混合し、100cc/分で窒素雰囲気を生成しながらジャケット付きスチールリアクター内の40℃の水200グラムに加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR415)および5.5グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちTBAEMA)を含む150グラムの水相2を加え、混合速度を1500rpmに上げる。混ぜ合わせた水相を60℃で60分間混合し、その後12.5グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(即ち2−(メタクリロイルオキシ)エチル]トリメチルアンモニウムクロライド)を含む150グラムの水相3を加え、混ぜ合わせた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間95℃に保持し、完全なポリマーを形成する。
ポリマー調製工程:水相1用に0.5グラムの水溶性開始剤(V50)を1000rpmで混合し、100cc/分で窒素雰囲気を生成しながらジャケット付きスチールリアクター内の40℃の水200グラムに加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。2.5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR415)および10グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちTBAEMA)を含む150グラムの水相2を加え、混合速度を1500rpmに上げる。混ぜ合わせた水相を60℃で60分間混合し、その後12.5グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(即ち2−(メタクリロイルオキシ)エチル]トリメチルアンモニウムクロライド)を含む150グラムの水相3を加え、混ぜ合わせた溶液を60℃でさらに30分間保持する。混ぜ合わせた水相を60℃で60分間混合し、その後12.5グラムのpHが6.0に調整された表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(2−スルホエチルメタクリレート)を含む150グラムの水相3を加え、混ぜ合わせた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間95℃に保持し、完全なポリマーを形成する。
ポリマー調製工程:水相1用に0.5グラムの水溶性開始剤(V50)を1000rpmで混合し、100cc/分で窒素雰囲気を生成しながらジャケット付きスチールリアクター内の40℃の水200グラムに加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。2.5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR9035またはSR502などのエトキシ化トリメチロ−ルプロパントリアクリレ−ト)および10グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちTBAEMA)を含む150グラムの水相2を加え、混合速度を1500rpmに上げる。混ぜ合わせた水相は60℃で60分間混合され、その後12.5グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(CD9055SR415)を含む150グラムの水相3を加え、その化合させた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間95℃に保持し、完全なポリマーを形成する。
ポリマー調製工程:水相1用に0.5グラムの水溶性開始剤(V50)を1000rpmで混合し、100cc/分で窒素雰囲気を生成しながらジャケット付きスチールリアクター内の40℃の水200グラムに加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。2.5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR344またはSR601などのポリエチエレングリコールジアクリレート)および10グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちTBAEMA)を含む150グラムの水相2を加え、混合速度を1500rpmに上げる。混ぜ合わせた水相は60℃で60分間混合され、その後12.5グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(CD9055SR415)を含む150グラムの水相3を加え、その化合させた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間95℃に保持し、完全なポリマーを形成する。
ポリマー調製工程:水相1用に0.5グラムの水溶性開始剤(V50)を1000rpmで混合し、100cc/分で窒素雰囲気を生成しながらジャケット付きスチールリアクター内の40℃の水200グラムに加える。溶液は45分間で40℃〜75℃へと加熱され、45分間75℃に保持され、75分間で60℃に冷やされる。2.5グラムの少なくとも1つの多官能水分散性アクリルモノマー(SR603などのポリエチレングリコールジメタクリレート)および10グラムの架橋性官能基を有する少なくとも1つの水溶性アクリルモノマー(即ちTBAEMA)を含む150グラムの水相2を加え、混合速度を1500rpmに上げる。混ぜ合わせた水相は60℃で60分間混合され、その後12.5グラムの表面電荷官能基を有する少なくとも1つの水溶性アクリルモノマー(CD9055SR415)を含む150グラムの水相3を加え、その混ぜ合わせた溶液を60℃でさらに30分間保持する。その後溶液を30分で75℃に加熱し、75℃から95℃に7時間で加熱し、6時間95℃に保持し、完全なポリマーを形成する。
マイクロカプセル懸濁液中の自由な油の特性評価:1グラムのマイクロカプセル懸濁液(40%固体)を10mlのヘキサン/DBP溶液と自動容量ディスペンサーを使用して混合し、マイクロカプセル懸濁液から遊離油を浸出させ、次にカウンターの上に30分置いた。上部の澄んだヘキサン/DBP層1mlを注意深くピペットで採取し、Agilent 6890N ガス・クロマトグラフィー(GC)によって評価し、懸濁液中の遊離な油を測定した。遊離な油の結果を下記表1に示す。
Claims (31)
- 表面電荷を有する壁を含むマイクロカプセルであって、
1つ以上の水相に開始剤、1つ以上の−OH、−NH2または−NH基を有する架橋性官能モノマーおよびカルボキシ基、スルホン酸基、4級アンモニウム基または他の帯電基から選択される1つ以上のアニオン性またはカチオン性基を有する帯電官能性モノマーを分散させることと、
その1つ以上の水相中でこれらモノマーを予備反応させ、水分散性多官能(メタ)アクリレートモノマーと混ぜ合わせることと、
混ぜ合わせたモノマーをさらに予備反応させることと、
高せん断撹拌を使用して前記1つ以上の水相中にイソシアネートと有益剤からなる芯材を含む油相を乳化させることによってエマルションを形成することと、
任意に追加でアミン架橋剤を加えることと、
予備反応させたモノマー、水分散性多官能(メタ)アクリレートモノマーおよび乳化させた油相を化合させたエマルションを有益剤からなる芯材を囲むマイクロカプセル壁を形成するのに充分な時間および温度で加熱するまたは充分な時間、化学線照射することによってさらに反応させることとを含む方法によって作製されるマイクロカプセル。 - 架橋性官能モノマーがアミンであることを特徴とする請求項1記載のマイクロカプセル。
- アミンがアルキルアミノアルキル(メタ)アクリレートであることを特徴とする請求項2記載のマイクロカプセル。
- 架橋性官能モノマーはヒドロキシル官能であることを特徴とする請求項1記載のマイクロカプセル。
- 架橋性官能モノマーはヒドロキシル(メタ)アクリレートであることを特徴とする請求項4記載のマイクロカプセル。
- 油溶性または油分散性有益剤からなる芯材とこの有益剤からなる芯材を囲むシェルとを含み、シェルはイソシアネートからなる第1成分およびアミンからなる第2成分から形成されるポリウレアを含み、アミンはアルキルアミノアルキル(メタ)アクリレートおよび多官能性(メタ)アクリレートとカルボキシアルキル(メタ)アクリレートまたは4級アンモニウムアクリレートとの反応生成物を含むマイクロカプセル。
- アミンはtert−ブチルアミノエチルメタクリレートであることを特徴とする請求項6記載のマイクロカプセル。
- シェルはイソシアネートと多官能性アミン(メタ)アクリレートの反応生成物を含むことを特徴とする請求項6記載のマイクロカプセル。
- イソシアネートはイソホロンジイソシアネート、4,4’−メチレンジフェニルジイソシアネート、2,2’−メチレンジフェニルジイソシアネートおよび2,4’−メチレンジフェニルジイソシアネートから選択されることを特徴とする請求項6記載のマイクロカプセル。
- アルキルアミノアルキル(メタ)アクリレートは各アルキル部分が独立してC1からC8のものが選択されることを特徴とする請求項6記載のマイクロカプセル。
- アルキルアミノ(メタ)アクリレートは、tert−ブチルアミノエチルメタクリレート、tert−ブチルアミノプロピルメタクリレート、 n−ブチルアミノエチルメタクリレート 、 ジエチルアミノエチルメタクリレート、ジメチルアミノエチルメタクリレート、ジイソプロピルアミノエチルメタクリレート、ジブチルアミノエチルメタクリレート、ジプロピルアミノエチルメタクリレート、tert−ペンチルアミノエチルメタクリレート、tert−ヘキシルアミノエチルメタクリレート、tert−ブチルアミノプロピルメタクリレート、ジエチルアミノプロピルメタクリレートおよびジメチルアミノプロピルメタクリレートから選択されることを特徴とする請求項6記載のマイクロカプセル。
- pH7で測定されたゼータ電位が+70〜−70であることを特徴とする請求項6記載のマイクロカプセル。
- 有益剤からなる芯材は、芳香剤、香水、相変化物質、生物活性物質、抗菌剤、自己修復組成物、潤滑剤または冷却剤の1つ以上から選択されることを特徴とする請求項6記載のマイクロカプセル。
- 油溶性または油分散性有益剤からなる芯材とこの有益剤からなる芯材を囲むシェルとを含み、シェルはイソシアネートおよび多官能性アミン(メタ)アクリレートとカルボキシアルキル(メタ)アクリレートの反応生成物を含み、多官能性アミン(メタ)アクリレートは極性のものが選択されるマイクロカプセル。
- 油溶性または油分散性有益剤からなる芯材とこの有益剤からなる芯材を囲むシェルとを含み、シェルはイソシアネートからなる第1成分およびポリオールからなる第2成分から形成されたポリウレタンを含み、ポリオールは、ヒドロキシル(メタ)アクリレートおよび多官能性(メタ)アクリレートとカルボキシアルキル(メタ)アクリレートまたは4級アンモニウムアクリレートの反応生成物を含むマイクロカプセル。
- ヒドロキシル(メタ)アクリレートはヒドロキシルエチル(メタ)アクリレートであることを特徴とする請求項15記載のマイクロカプセル。
- シェルはイソシアネートと多官能性ヒドロキシル(メタ)アクリレートの反応生成物を含むことを特徴とする請求項15記載のマイクロカプセル。
- イソシアネートは、イソホロンジイソシアネート、4,4’−メチレンジフェニルジイソシアネート、2,2’−メチレンジフェニルジイソシアネートおよび2,4’−メチレンジフェニルジイソシアネートから選択されることを特徴とする請求項15記載のマイクロカプセル。
- ヒドロキシアルキル(メタ)アクリレートのアルキル部分がC1からC24のものが選択されることを特徴とする請求項15記載のマイクロカプセル。
- ヒドロキシル(メタ)アクリレートは、ヒドロキシアルキル(メタ)アクリレート、アルキレングリコール(メタ)アクリレート、アルキレングリコール(メタ)アクリレートおよびグリセロール1,3−ジグリセレートジアクリレートから選択されることを特徴とする請求項15記載のマイクロカプセル。
- pH7で測定されたゼータ電位が+70〜−70であることを特徴とする請求項15記載のマイクロカプセル。
- 有益剤からなる芯材は、芳香剤、香水、相変化物質、生物活性物質、抗菌剤、自己修復組成物、潤滑剤または冷却剤の1つ以上から選択されることを特徴とする請求項15記載のマイクロカプセル。
- 油溶性または油分散性有益剤からなる芯材とこの有益剤からなる芯材を囲むシェルとを含み、シェルはイソシアネートおよび多官能性ポリオール(メタ)アクリレートとカルボキシアルキル(メタ)アクリレートの反応生成物を含み、多官能性ポリオール(メタ)アクリレートは極性のものが選択されることを特徴とするマイクロカプセル。
- 有益剤デリバリー粒子の製造方法であって、この方法は、
水と開始剤を含む水相1と水と水溶性または水分散性アミン(メタ)アクリレートまたはヒドロキシル(メタ)アクリレートおよび水溶性または水分散性多官能(メタ)アクリレートとを含む架橋性官能モノマーとを含む水相2とを混ぜ合わせ、
混ぜ合わせた水相のアミン(メタ)アクリレートまたはヒドロキシル(メタ)アクリレートと多官能(メタ)アクリレートを予備反応させて多官能アミン(メタ)アクリレートまたはヒドロキシル(メタ)アクリレートプレポリマーを形成し、
このプレポリマーを水と、カルボキシアルキル(メタ)アクリレートと、塩基または4級アンモニウムアルキルアクリレートとを含む水相3と混ぜ合わせ、
この混ぜ合わせたプレポリマーをさらに予備反応させて第1の組成物を供することと、
イソシアネートと有益剤からなる芯材とを含む油相を含む第2組成物を第1の組成物内に高せん断撹拌下で乳化することによってエマルションを形成することと、
任意にさらにアミン架橋剤を加えることと、
1つ以上の工程で前記エマルションを加熱し、イソシアネートと前記プレポリマーの反応生成物を含み、前記有益剤からなる芯材を囲む壁材を形成することとを含む有益剤デリバリー粒子の製造方法。 - マイクロカプセルはpH7で測定されたゼータ電位が+70〜−70であることを特徴とする請求項24記載の方法。
- アミン(メタ)アクリレートは、アルキルアミノアルキル(メタ)アクリレートであり、各アルキル部分は独立してC1からC8であることを特徴とする請求項24記載の方法。
- 有益剤デリバリー粒子の製造方法であって、この方法は、
水と開始剤を含む水相1と水と水溶性または水分散性ヒドロキシル(メタ)アクリレートおよび水溶性または水分散性多官能(メタ)アクリレートとを含む架橋性官能モノマーとを含む水相2とを混ぜ合わせ、
混ぜ合わせた水相のアミン(メタ)アクリレートまたはヒドロキシル(メタ)アクリレートと多官能(メタ)アクリレートを予備反応させてヒドロキシ(メタ)アクリレートプレポリマーを形成し、
このプレポリマーを、水とカルボキシアルキル(メタ)アクリレートと、塩基または4級アンモニウムアルキルアクリレートとを含む水相3と混ぜ合わせ、
この混ぜ合わせたプレポリマーをさらに予備反応させて第1の組成物を供することと、
イソシアネートと有益剤からなる芯材とを含む油相を含む第2組成物を第1の組成物内に高せん断撹拌下で乳化することによってエマルションを形成することと、
任意にさらにアミン架橋剤を加えることと、
1つ以上の工程で前記エマルションを加熱し、イソシアネートと前記プレポリマーの反応生成物を含み、前記有益剤からなる芯材を囲む壁材を形成することとを含む有益剤デリバリー粒子の製造方法。 - マイクロカプセルはpH7で測定されたゼータ電位が+70〜−70であることを特徴とする請求項27記載の方法。
- アミン(メタ)アクリレートは、アルキルアミノアルキル(メタ)アクリレートであり、各アルキル部分は独立してC1からC8であることを特徴とする請求項27記載の方法。
- ヒドロキシル(メタ)アクリレートはヒドロキシアルキル(メタ)アクリレート、アルキレングリコール(メタ)アクリレート、アルキレングリコール(メタ)アクリレートおよびグリセロール1,3−ジグリセレートジアクリレートから選択されることを特徴とする請求項27記載の方法。
- マイクロカプセルはpH7で測定されたゼータ電位が+40より高い正の値または−40より大きい負の値であることを特徴とする請求項27記載の方法。
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JP2015163710A (ja) * | 2010-04-28 | 2015-09-10 | ザ プロクター アンド ギャンブルカンパニー | 送達粒子 |
JP2013538882A (ja) * | 2010-07-15 | 2013-10-17 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 有益剤送達粒子、前記粒子を調製するための方法、前記粒子を含む組成物および基質を処理するための方法 |
WO2012075293A2 (en) * | 2010-12-01 | 2012-06-07 | Isp Investments Inc. | Hydrogel microcapsules |
WO2015023961A1 (en) * | 2013-08-15 | 2015-02-19 | International Flavors & Fragrances Inc. | Polyurea or polyurethane capsules |
CN104693774A (zh) * | 2015-03-11 | 2015-06-10 | 东华大学 | 一种具有芳香气味的聚乙二醇双丙烯酸酯水凝胶及其制备方法 |
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JP2020515657A (ja) * | 2018-03-13 | 2020-05-28 | ザ プロクター アンド ギャンブル カンパニーThe Procter & Gamble Company | マイクロカプセルを含む消費者製品組成物 |
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WO2017074997A1 (en) | 2017-05-04 |
EP3368207A4 (en) | 2019-05-08 |
WO2017074995A1 (en) | 2017-05-04 |
CA2996668C (en) | 2023-09-26 |
US20180235893A1 (en) | 2018-08-23 |
CN107708853A (zh) | 2018-02-16 |
US20170113200A1 (en) | 2017-04-27 |
EP3368207B1 (en) | 2021-12-01 |
EP3390483B1 (en) | 2022-05-18 |
US10864167B2 (en) | 2020-12-15 |
EP3390483A4 (en) | 2019-06-19 |
JP6911014B2 (ja) | 2021-07-28 |
EP3368207A1 (en) | 2018-09-05 |
CN107708853B (zh) | 2021-12-07 |
US9937477B2 (en) | 2018-04-10 |
EP3390483A1 (en) | 2018-10-24 |
CA2996668A1 (en) | 2017-05-04 |
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