JP5364305B2 - Aroma-sustaining microcapsule - Google Patents
Aroma-sustaining microcapsule Download PDFInfo
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- JP5364305B2 JP5364305B2 JP2008162818A JP2008162818A JP5364305B2 JP 5364305 B2 JP5364305 B2 JP 5364305B2 JP 2008162818 A JP2008162818 A JP 2008162818A JP 2008162818 A JP2008162818 A JP 2008162818A JP 5364305 B2 JP5364305 B2 JP 5364305B2
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- fragrance
- microcapsule
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- alcoholic
- silicate
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- 239000003094 microcapsule Substances 0.000 title claims abstract description 54
- 239000003205 fragrance Substances 0.000 claims abstract description 89
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 46
- -1 silicic acid ester Chemical class 0.000 claims abstract description 38
- 239000002304 perfume Substances 0.000 claims abstract description 5
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 27
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003995 emulsifying agent Substances 0.000 claims description 15
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 12
- 239000005792 Geraniol Substances 0.000 claims description 12
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 12
- 229940113087 geraniol Drugs 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 claims description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 2
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 claims description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 2
- 235000000484 citronellol Nutrition 0.000 claims description 2
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 claims description 2
- 229940041616 menthol Drugs 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims 2
- KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 claims 1
- AZUVBPVDRHGGEP-UHFFFAOYSA-N 6a,9a-dimethyl-4,5,7,8,9,9a-hexahydro-6aH-dipyrrolo(2,3-b;3',2',1'-hi)indole Natural products CC(=C)C1CCC(C)=CCCC(C)=CCCC(C)=CC1O AZUVBPVDRHGGEP-UHFFFAOYSA-N 0.000 claims 1
- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 claims 1
- 230000002045 lasting effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 29
- 125000000217 alkyl group Chemical group 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- 239000000796 flavoring agent Substances 0.000 description 7
- 235000019634 flavors Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000011162 core material Substances 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 230000037330 wrinkle prevention Effects 0.000 description 2
- 150000000215 1-octanols Chemical class 0.000 description 1
- PUNGSQUVTIDKNU-UHFFFAOYSA-N 2,4,6,8,10-pentamethyl-1,3,5,7,9,2$l^{3},4$l^{3},6$l^{3},8$l^{3},10$l^{3}-pentaoxapentasilecane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O[Si](C)O1 PUNGSQUVTIDKNU-UHFFFAOYSA-N 0.000 description 1
- BKMUDUXPSVRLFZ-UHFFFAOYSA-N 2-methyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane Chemical compound C[SiH]1O[SiH2]O[SiH2]O[SiH2]O[SiH2]O1 BKMUDUXPSVRLFZ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- ZUBMAQBMOHLPFU-UHFFFAOYSA-N C1(=CC=CC=C1)CCO[Si](CCCCCCCCCC)(OCCC1=CC=CC=C1)OCCC1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)CCO[Si](CCCCCCCCCC)(OCCC1=CC=CC=C1)OCCC1=CC=CC=C1 ZUBMAQBMOHLPFU-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MAZJFWHKKPFVND-UHFFFAOYSA-N aluminum propan-2-ol propan-2-olate Chemical compound [Al+3].CC(C)O.CC(C)[O-].CC(C)[O-].CC(C)[O-] MAZJFWHKKPFVND-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- BAAAEEDPKUHLID-UHFFFAOYSA-N decyl(triethoxy)silane Chemical compound CCCCCCCCCC[Si](OCC)(OCC)OCC BAAAEEDPKUHLID-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- OIYVLSMPJCJTEX-UHFFFAOYSA-N tetrakis(2-phenylethyl) silicate Chemical compound C=1C=CC=CC=1CCO[Si](OCCC=1C=CC=CC=1)(OCCC=1C=CC=CC=1)OCCC1=CC=CC=C1 OIYVLSMPJCJTEX-UHFFFAOYSA-N 0.000 description 1
- UXPNNKCIEHKAAV-NISPWTRESA-N tetrakis[(2e)-3,7-dimethylocta-2,6-dienyl] silicate Chemical compound CC(C)=CCC\C(C)=C\CO[Si](OC\C=C(/C)CCC=C(C)C)(OC\C=C(/C)CCC=C(C)C)OC\C=C(/C)CCC=C(C)C UXPNNKCIEHKAAV-NISPWTRESA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
本発明は、香気を有するアルコール(以下アルコール性香料という)の香り持続性、残香性に優れたマイクロカプセル、及びこのマイクロカプセルを含有する組成物に関する。 The present invention relates to a microcapsule excellent in fragrance persistence and residual fragrance of a scented alcohol (hereinafter referred to as alcoholic fragrance), and a composition containing the microcapsule.
従来、乳液、化粧液、化粧水、美容液、クリーム、ジェル製剤、毛髪処理剤、医薬部外品等の香粧品組成物、柔軟剤、しわ防止スプレー等の繊維処理剤組成物、紙おむつ等の衛生用品組成物、芳香剤組成物などには芳香の賦与や不快臭のマスキングなどを目的として香料が使用されている。 Conventionally, cosmetics such as milky lotion, cosmetic liquid, lotion, cosmetic liquid, cream, gel preparation, hair treatment agent, quasi-drug, softener, fiber treatment composition such as wrinkle prevention spray, paper diaper, etc. Fragrances are used in sanitary ware compositions, fragrance compositions and the like for the purpose of imparting fragrance and masking unpleasant odors.
このような組成物に使用される香料は、香りの持続性、残香性を目的として香料をマイクロカプセル化して配合する試みがなされている。 The fragrance | flavor used for such a composition is made the trial which mix | blends and mix | blends the fragrance | flavor with the objective of the fragrance sustainability and the remaining fragrance property.
香料のマイクロカプセルは、芯物質の香料を壁材で包んだ球状物質であり、その役割は芯物質の香料を保護し、カプセルに物理的な力が加わった際にカプセルの壁が破れて芯物質の香料を放出するものである。 The fragrance microcapsule is a spherical substance that is made by wrapping the fragrance of the core material with a wall material. Its role is to protect the fragrance of the core material, and when the capsule is subjected to physical force, the capsule wall breaks and the core It releases the fragrance of the substance.
特許文献1には、芯物質として引火点が50〜130℃の範囲内の香料組成物を含有するカプセル化香料が記載されている。また、引用文献2には、高揮発性香料等の揮発成分と、それよりも高融点で相溶性がある添加剤を含有するマイクロカプセルが記載されている。 Patent Document 1 describes an encapsulated fragrance containing a fragrance composition having a flash point of 50 to 130 ° C. as a core substance. Reference 2 describes a microcapsule containing a volatile component such as a highly volatile fragrance and an additive having a higher melting point and compatibility.
しかし、従来の香料を含有するマイクロカプセルはカプセル壁が崩壊した直後は香料の香り立ちに優れるが、速やかに揮散、消失するため残香性に課題があり、特に低分子量で親水性の高いアルコール性香料にその傾向が顕著であった。 However, microcapsules containing conventional fragrances are excellent in fragrance perfume immediately after the capsule wall collapses, but have problems with residual fragrance because they volatilize and disappear quickly, especially with low molecular weight and high hydrophilicity The tendency was remarkable in the fragrance.
更に親水性の高いアルコール性香料を用いて乳化系でマイクロカプセルを製造する場合、カプセル外の水相に香料が流出してしまい、アルコール性香料を内包するマイクロカプセルを製造できないという問題もあった。
本発明の課題は、マイクロカプセル壁の崩壊後、アルコール性香料の香りを持続させて、残香性を向上させ、しかも従来はマイクロカプセル化が困難であった親水性の高いアルコール性香料であっても、カプセル内への内包を可能にするマイクロカプセル及びそれを含有する組成物を提供することにある。 An object of the present invention is to maintain a fragrance of an alcoholic fragrance after disintegration of a microcapsule wall, to improve a residual fragrance, and to be a highly hydrophilic alcoholic fragrance that has conventionally been difficult to be microencapsulated. It is another object of the present invention to provide a microcapsule that can be encapsulated in a capsule and a composition containing the same.
本発明者は、上記課題を解決するため鋭意検討を行った結果、アルコール性香料をケイ酸エステル化した後にマイクロカプセル中に内包させることにより、水溶性の高いアルコール性香料であっても容易にマイクロカプセル化することが可能であり、更にはマイクロカプセルに物理的な力が加わって壁が崩壊した後に、アルコール性香料のケイ酸エステルが水分で徐々に分解し、アルコール性香料を放出することで香りを持続させ、残香性を向上させることを見出した。 As a result of intensive studies to solve the above-mentioned problems, the present inventor easily converts alcoholic fragrance into a silicate ester and then encapsulates it in a microcapsule, so that even a highly water-soluble alcoholic fragrance can be easily obtained. It can be microencapsulated, and after the wall is collapsed due to physical force applied to the microcapsule, the alcoholic fragrant silicate is gradually decomposed with moisture to release the alcoholic fragrance. It was found that the scent is maintained and the residual fragrance is improved.
即ち本発明は、アルコール性香料のケイ酸エステルを含有するマイクロカプセル、及びこのマイクロカプセルを含有する組成物を提供する。 That is, this invention provides the microcapsule containing the silicate ester of alcoholic fragrance | flavor, and the composition containing this microcapsule.
本発明により、水溶性の高いアルコール性香料であっても容易にマイクロカプセル化することが可能となり、アルコール性香料の香りを持続させて、残香性に優れたマイクロカプセルを提供することができた。 According to the present invention, even a highly water-soluble alcoholic fragrance can be easily microencapsulated, and the scent of the alcoholic fragrance can be maintained to provide a microcapsule having excellent residual fragrance properties. .
[アルコール性香料のケイ酸エステル]
本発明のアルコール性香料のケイ酸エステルを構成するアルコール性香料は、「香料と調香の基礎知識,中島基貴 編著、産業図書」に例示される分子内に水酸基を含む香料であり、単品、混合物のどちらを用いてもよい。本発明に用いられるアルコール性香料としては、CLogP値が4以下のものが好ましい。CLogP値が4以下のアルコール性香料の例としては次の香料が挙げられる(括弧内はClogP値)。
[Silicate ester of alcoholic fragrance]
The alcoholic fragrance constituting the silicate ester of the alcoholic fragrance of the present invention is a fragrance containing a hydroxyl group in the molecule exemplified in “Basic knowledge of fragrance and fragrance, edited by Motoki Nakajima, Industrial Books”. Either of the mixtures may be used. The alcoholic fragrance used in the present invention preferably has a CLogP value of 4 or less. The following fragrance | flavors are mentioned as an example of the alcoholic fragrance | flavor whose CLogP value is 4 or less (a ClogP value is in a parenthesis).
フェニルエチルアルコール(1.33)、ゲラニオール(2.97)、ネロール(2.97)、シトロネロール(3.25)、テトラヒドロゲラニオール(3.74)、cis−3−ヘキセノール(1.40)、フェニルヘキサノール(3.17)、メントール(3.23)、アニスアルコール(1.10)、マヨール(2.53)。 Phenylethyl alcohol (1.33), geraniol (2.97), nerol (2.97), citronellol (3.25), tetrahydrogeraniol (3.74), cis-3-hexenol (1.40), phenylhexanol (3.17), menthol (3.23), anis alcohol (1.10), Mayor (2.53).
なお、CLogP値は有機化合物の水と1−オクタノールに対する親和性を示す係数であり、この1−オクタノール/水分配係数Pは、1−オクタノールと水の2液相の溶媒に微量の化合物が溶質として溶け込んだときの分配平衡で、それぞれの溶媒中における化合物の平衡濃度の比であり、底10に対するそれらの対数LogPの形で示すのが一般的である。Daylight CISから入手できるプログラム“CLOGP”で計算すると最も便利である。このプログラムは、実測のLogP値がある場合にはそれと伴に、Hansch, Leoのフラグメントアプローチにより算出されるCLogPの値を出力する。フラグメントアプローチは化合物の化学構造に基づいており、原子の数及び化学結合のタイプを考慮している(cf. A. Leo, Comprehensive Medicinal Chemistry, Vol.4, C. Hansch, P.G. Sammens, J.B. Taylor and C.A. Ramsden, Eds., p.295, Pergamon Press, 1990)。このCLogP値は現在最も汎用的で信頼できる推定値であり、本発明ではプログラムCLOGP v4.01により計算したCLogP値を用いる。 The CLogP value is a coefficient indicating the affinity of an organic compound for water and 1-octanol, and this 1-octanol / water partition coefficient P is a solute of a small amount of compound in a two-liquid solvent of 1-octanol and water. Is the distribution equilibrium when dissolved as the ratio of the equilibrium concentration of the compounds in each solvent, and is generally shown in the form of their logarithm LogP relative to the base 10. It is most convenient to calculate with the program “CLOGP” available from Daylight CIS. This program outputs the value of CLogP calculated by Hansch, Leo's fragment approach together with the measured LogP value, if any. The fragment approach is based on the chemical structure of the compound and takes into account the number of atoms and the type of chemical bond (cf. A. Leo, Comprehensive Medicinal Chemistry, Vol. 4, C. Hansch, PG Sammens, JB Taylor and CA Ramsden, Eds., P.295, Pergamon Press, 1990). This CLogP value is the most general and reliable estimate at present, and the present invention uses the CLogP value calculated by the program CLOGP v4.01.
本発明に用いられるアルコール性香料のケイ酸エステルとしては、下記式(1)〜(3)で表される化合物が挙げられる。 Examples of the silicate ester of an alcoholic fragrance used in the present invention include compounds represented by the following formulas (1) to (3).
〔式中、R1はアルコール性香料から水酸基1個を除いた残基、R2及びR3はそれぞれ独立に、置換基としてフェニル基、水酸基又はアルコキシ基を有していても良い総炭素数1〜22の炭化水素基、−OR4又は−OSi(R5)3を示し、R4は炭素数1〜22の炭化水素基又はアルコール性香料から水酸基1個を除いた残基、R5は置換基としてフェニル基、水酸基又はアルコキシ基を有していても良い総炭素数1〜22の炭化水素基又は−OR4を示す。nは平均値を示す2以上の数、mは平均値を示す0以上の数であり、複数個のR1、R2、R3及びR5はそれぞれ同一でも異なっていても良い。〕
一般式(1)〜(3)において、アルコール性香料から水酸基1個を除いた残基を形成するアルコール性香料としては、上記のCLogP値が4以下のアルコール性香料が好ましい。
[Wherein R 1 is a residue obtained by removing one hydroxyl group from an alcoholic fragrance, and R 2 and R 3 are each independently a total carbon number optionally having a phenyl group, a hydroxyl group or an alkoxy group as a substituent. 1 to 22 hydrocarbon group, —OR 4 or —OSi (R 5 ) 3 , wherein R 4 is a hydrocarbon group having 1 to 22 carbon atoms or a residue obtained by removing one hydroxyl group from an alcoholic fragrance, R 5 Represents a hydrocarbon group having 1 to 22 carbon atoms which may have a phenyl group, a hydroxyl group or an alkoxy group as a substituent, or —OR 4 . n is a number of 2 or more showing an average value, m is a number of 0 or more showing an average value, and a plurality of R 1 , R 2 , R 3 and R 5 may be the same or different. ]
In the general formulas (1) to (3), as the alcoholic fragrance forming the residue obtained by removing one hydroxyl group from the alcoholic fragrance, the above-mentioned alcoholic fragrance having a CLogP value of 4 or less is preferable.
一般式(1)において、R2は、置換基としてフェニル基、水酸基又はアルコキシ基を有していても良い総炭素数1〜22の直鎖又は分岐鎖のアルキル基又はアルケニル基、あるいは−OR4が好ましく、総炭素数1〜22の直鎖又は分岐鎖のアルキル基又はアルケニル基としては、炭素数6〜18の直鎖又は分岐鎖のアルキル基が好ましく、n−ヘキシル基、n−オクチル基、n−デシル基、n−ドデシル基、n−ヘキサデシル基、n−オクタデシル基等の炭素数6〜18の直鎖アルキル基が更に好ましく、炭素数8〜18の直鎖アルキル基が更により好ましい。R4は炭素数1〜6の炭化水素基又はアルコール性香料から水酸基1個を除いた残基が好ましく、炭素数1〜3のアルキル基又はアルコール性香料から水酸基1個を除いた残基がより好ましい。 In the general formula (1), R 2 is a linear or branched alkyl or alkenyl group having 1 to 22 carbon atoms which may have a phenyl group, a hydroxyl group or an alkoxy group as a substituent, or —OR 4 is preferable, and the linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms is preferably a linear or branched alkyl group having 6 to 18 carbon atoms, and includes n-hexyl group and n-octyl group. A straight chain alkyl group having 6 to 18 carbon atoms such as a group, n-decyl group, n-dodecyl group, n-hexadecyl group, n-octadecyl group, etc. is more preferred, and a straight chain alkyl group having 8 to 18 carbon atoms is even more preferred. preferable. R 4 is preferably a residue obtained by removing one hydroxyl group from a hydrocarbon group having 1 to 6 carbon atoms or an alcoholic fragrance, and a residue obtained by removing one hydroxyl group from an alkyl group having 1 to 3 carbon atoms or an alcoholic fragrance. More preferred.
一般式(2)及び(3)において、R3は置換基としてフェニル基、水酸基又はアルコキシ基を有していても良い総炭素数1〜22の直鎖又は分岐鎖のアルキル基又はアルケニル基、あるいは−OR4が好ましく、総炭素数1〜22の直鎖又は分岐鎖のアルキル基又はアルケニル基としては、炭素数1〜6の直鎖又は分岐鎖のアルキル基又はアルケニル基が好ましく、炭素数1〜3のアルキル基がより好ましい。R4は炭素数1〜6の炭化水素基又はアルコール性香料から水酸基1個を除いた残基が好ましく、炭素数1〜3のアルキル基又はアルコール性香料から水酸基1個を除いた残基がより好ましい。nは平均値を示す2以上の数、mは平均値を示す0以上の数であり、nとmの和が2〜16となる数が好ましく、2〜10がより好ましく、2〜6が更に好ましい。 In the general formulas (2) and (3), R 3 is a linear or branched alkyl or alkenyl group having 1 to 22 carbon atoms which may have a phenyl group, a hydroxyl group or an alkoxy group as a substituent, Alternatively preferably -OR 4, as the total linear or branched alkyl or alkenyl group having a carbon number of 1 to 22, preferably an alkyl or alkenyl group of a straight-chain or branched-chain having 1 to 6 carbon atoms, carbon atoms 1-3 alkyl groups are more preferred. R 4 is preferably a residue obtained by removing one hydroxyl group from a hydrocarbon group having 1 to 6 carbon atoms or an alcoholic fragrance, and a residue obtained by removing one hydroxyl group from an alkyl group having 1 to 3 carbon atoms or an alcoholic fragrance. More preferred. n is a number of 2 or more showing an average value, m is a number of 0 or more showing an average value, a number in which the sum of n and m is 2 to 16, preferably 2 to 10, more preferably 2 to 6, Further preferred.
これらのアルコール性香料のケイ酸エステルは、公知の合成法により得ることができ、例えば下記の方法1,2等が挙げられる。
方法1:
テトラアルコキシ(アルコキシ基の炭素数1〜22)シラン、アルキル(アルキル基の炭素数1〜22)トリアルコキシ(アルコキシ基の炭素数1〜22)シラン、ジアルキル(アルキル基の炭素数1〜22)ジアルコキシ(アルコキシ基の炭素数1〜22)シラン等のアルコキシモノシラン類、あるいはアルコキシ基(アルコキシ基の炭素数1〜22)を有する直鎖状又は環状のポリシロキサン類と、アルコール性香料とのエステル交換反応。
方法2:
テトラクロロシラン、アルキル(アルキル基の炭素数1〜22)トリクロロシラン等のハロゲン化モノシラン類、あるいは直鎖状又は環状のハロゲン化ポリシロキサン類と、アルコール性香料とのエステル化反応。
Silicate esters of these alcoholic fragrances can be obtained by a known synthesis method, and examples thereof include the following methods 1 and 2.
Method 1:
Tetraalkoxy (alkoxy group having 1 to 22 carbon atoms) silane, alkyl (alkyl group having 1 to 22 carbon atoms) trialkoxy (alkoxy group having 1 to 22 carbon atoms) silane, dialkyl (alkyl group having 1 to 22 carbon atoms) Alkoxy monosilanes such as dialkoxy (alkoxy group having 1 to 22 carbon atoms) silane, or linear or cyclic polysiloxane having an alkoxy group (alkoxy group having 1 to 22 carbon atoms), and alcoholic fragrance Transesterification reaction.
Method 2:
Esterification reaction of halogenated monosilanes such as tetrachlorosilane, alkyl (alkyl group having 1 to 22 carbon atoms) trichlorosilane, or linear or cyclic halogenated polysiloxanes with an alcoholic fragrance.
これらの方法の中では方法1が好ましい。方法1において、エステル交換されるアルコキシ基としては、入手性等の点からメトキシ基又はエトキシ基が好ましく、エトキシ基がより好ましい。 Of these methods, Method 1 is preferred. In Method 1, the alkoxy group to be transesterified is preferably a methoxy group or an ethoxy group, more preferably an ethoxy group from the viewpoint of availability.
方法1のアルコキシモノシラン又はポリシロキサンとアルコール性香料とのエステル交換反応において、アルコキシモノシラン又はポリシロキサンに対して加えるアルコール性香料のモル比により置換度が異なる反応物を与え、アルコキシモノシラン又はポリシロキサンのアルコキシ基1個に対するアルコール性香料の割合は、10〜500モル%が好ましく、50〜150モル%がより好ましい。 In the transesterification reaction between the alkoxymonosilane or polysiloxane and the alcoholic fragrance in Method 1, a reactant having a different substitution degree is provided depending on the molar ratio of the alcoholic fragrance added to the alkoxymonosilane or polysiloxane. 10-500 mol% is preferable and, as for the ratio of the alcoholic fragrance | flavor with respect to one alkoxy group, 50-150 mol% is more preferable.
方法1におけるエステル交換反応の反応温度は、アルコキシモノシラン又はポリシロキサン及びアルコール性香料の沸点以下が好ましく、室温(20℃)〜200℃がより好ましく、50〜170℃が更に好ましく、70〜150℃が更により好ましく、90〜130℃が特に好ましい。 The reaction temperature of the transesterification reaction in Method 1 is preferably not more than the boiling point of the alkoxymonosilane or polysiloxane and the alcoholic fragrance, more preferably from room temperature (20 ° C.) to 200 ° C., further preferably from 50 to 170 ° C., more preferably from 70 to 150 ° C. Is more preferable, and 90 to 130 ° C. is particularly preferable.
方法1におけるエステル交換反応は、減圧下で行うことが、反応を速やかに進行させることができる等の点から好ましい。減圧度は反応温度にもよるが、アルコキシモノシラン又はポリシロキサン及びアルコール性香料の沸点以下で行えばよく、1.3Pa〜常圧(0.1MPa)が好ましく、130Pa〜40kPaがより好ましく、1.3kPa〜13kPaが更に好ましい。反応は反応初期から減圧下で行っても、途中から減圧下で行っても良い。 The transesterification reaction in Method 1 is preferably performed under reduced pressure from the viewpoint that the reaction can proceed rapidly. Although the degree of vacuum depends on the reaction temperature, it may be carried out below the boiling point of alkoxymonosilane or polysiloxane and alcoholic fragrance, preferably 1.3 Pa to normal pressure (0.1 MPa), more preferably 130 Pa to 40 kPa. 3 kPa to 13 kPa is more preferable. The reaction may be performed under reduced pressure from the beginning of the reaction or under reduced pressure from the middle.
方法1におけるエステル交換反応は、触媒を添加することが、反応を速やかに進行させることができる等の点から好ましい。触媒としては、水酸化ナトリウム、水酸化カリウム、ナトリウムメトキシド、ナトリウムエトキシド、カリウムメトキシド、カリウムエトキシド等のアルカリ触媒や、アルミニウムテトライソプロポキシド、チタンテトライソプロポキシド等のルイス酸触媒を用いることができる。 In the transesterification reaction in Method 1, it is preferable to add a catalyst from the viewpoint that the reaction can proceed rapidly. Examples of the catalyst include alkali catalysts such as sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, and Lewis acid catalysts such as aluminum tetraisopropoxide and titanium tetraisopropoxide. Can be used.
方法1のエステル交換反応、方法2のエステル化反応で得られるアルコール性香料のケイ酸エステルは、他に置換度の異なる混合物があっても、さらにシロキサンが縮合した鎖状または環状の重・縮合物との混合物であっても良い。また、方法1のエステル交換反応、方法2におけるエステル化反応は、2種以上のアルコール性香料を混合して用いても、2種以上のアルコキシモノシラン又はポリシロキサン、あるいはハロゲン化モノシラン又はポリシロキサンを用いても良い。 Silicate esters of alcoholic fragrances obtained by the ester exchange reaction of Method 1 and the esterification reaction of Method 2 may be a chain or cyclic polycondensation in which a siloxane is further condensed even if there are other mixtures having different degrees of substitution. It may be a mixture with a product. Further, the transesterification reaction in Method 1 and the esterification reaction in Method 2 can be carried out by mixing two or more alcoholic fragrances and using two or more alkoxymonosilanes or polysiloxanes, or halogenated monosilanes or polysiloxanes. It may be used.
[マイクロカプセル]
本発明のマイクロカプセルは、芯剤としてアルコール性香料のケイ酸エステルを含有するものであり、香料そのもの、酸化防止剤、油剤等の他の任意成分を芯剤として含んでもよい。
[Microcapsule]
The microcapsule of the present invention contains a silicate ester of an alcoholic fragrance as a core, and may contain other optional components such as the fragrance itself, an antioxidant, and an oil as a core.
本発明のマイクロカプセル中のアルコール性香料のケイ酸エステルの含有量は用途により変動するものであるが、通常は10〜99重量%の範囲が好ましい。 The content of the silicate ester of the alcoholic fragrance in the microcapsule of the present invention varies depending on the use, but is usually preferably in the range of 10 to 99% by weight.
本発明のマイクロカプセルの調製法は特に制限されず、公知のマイクロカプセル化方法を採用することができる。具体的には化学的製法(界面重合法、in situ重合法、オリフィス法)、物理化学的方法(コアセルベーション法)、機械的・物理的方法(気中懸濁被覆法、噴霧乾燥法、高速気流中衝撃法)等が挙げられる。マイクロカプセルの壁材としてはポリウレア、ポリウレタン、ポリアミド、メラミン樹脂、尿素樹脂、アルギン酸塩、ゼラチン、アラビアゴム、デンプン等の各種高分子化合物が挙げられる。 The method for preparing the microcapsules of the present invention is not particularly limited, and a known microencapsulation method can be employed. Specifically, chemical production methods (interfacial polymerization method, in situ polymerization method, orifice method), physicochemical methods (coacervation method), mechanical / physical methods (air suspension coating method, spray drying method, High-speed air-flow impact method). Examples of the microcapsule wall material include various polymer compounds such as polyurea, polyurethane, polyamide, melamine resin, urea resin, alginate, gelatin, gum arabic, and starch.
本発明のマイクロカプセルの製造方法についてより具体的には、造る+使うマイクロカプセル(工業調査会)、特開2008−63575号公報、特開2006−249326号公報、特開平11−216354号公報、特開平5−222672号公報等に記載されている方法を採用することができる。 More specifically, the manufacturing method of the microcapsules of the present invention is the microcapsules to be manufactured and used (Industry Research Committee), JP 2008-63575 A, JP 2006-249326 A, JP 11-216354 A, A method described in JP-A-5-222672 and the like can be employed.
本発明のマイクロカプセルの好ましい製造方法としては、エチレン−無水マレイン酸共重合体等の乳化剤とアルコール性香料のケイ酸エステルを水中に分散させて乳化物を得た後、この乳化物にメラミン−ホルムアルデヒド樹脂等の壁材を添加して撹拌することによりマイクロカプセルのスラリーを得る方法;予め壁材を形成するモノマーとエチレン−無水マレイン酸共重合体等の乳化剤を水中で混合して、壁材・乳化剤混合物を調製した後、この壁材・乳化剤混合物とアルコール性香料のケイ酸エステルとを乳化し、この乳化物にホルムアルデヒドを添加して撹拌することによりマイクロカプセルのスラリーを得る方法等が挙げられる。 As a preferred method for producing the microcapsules of the present invention, an emulsifier such as an ethylene-maleic anhydride copolymer and an alcoholic fragrance silicate ester are dispersed in water to obtain an emulsion, and then the melamine- A method of obtaining a microcapsule slurry by adding and stirring a wall material such as formaldehyde resin; a wall material by previously mixing a monomer that forms the wall material and an emulsifier such as an ethylene-maleic anhydride copolymer in water -After preparing the emulsifier mixture, emulsify this wall material / emulsifier mixture and silicate ester of alcoholic fragrance, add formaldehyde to this emulsion, and stir the microcapsule slurry. It is done.
本発明のマイクロカプセルは、乳液、化粧液、化粧水、美容液、クリーム、ジェル製剤、毛髪処理剤、医薬部外品等の香粧品、柔軟剤、しわ防止スプレー等の繊維処理剤、紙おむつのような衛生用品、芳香剤などの各種用途に好適に用いることができる。 The microcapsules of the present invention include emulsions, cosmetics, lotions, cosmetics, creams, gel preparations, hair treatments, cosmetics such as quasi-drugs, softeners, fiber treatments such as wrinkle prevention sprays, and paper diapers. It can use suitably for various uses, such as sanitary goods and a fragrance | flavor.
[組成物]
本発明のマイクロカプセルを含有する組成物は、洗浄剤組成物、柔軟剤組成物等の繊維処理剤組成物、香粧品組成物、芳香剤組成物、消臭剤組成物等として用いることができ、繊維処理剤組成物として用いるのが好ましい。
[Composition]
The composition containing the microcapsules of the present invention can be used as a fiber treatment agent composition such as a detergent composition and a softener composition, a cosmetic composition, a fragrance composition, a deodorant composition, and the like. The fiber treatment agent composition is preferably used.
本発明の組成物中のマイクロカプセルの含有量は、特に限定されずその用途により種々変えることができる。本発明の組成物を洗浄剤組成物や柔軟剤組成物等の繊維処理剤組成物として用いる場合、組成物中の本発明のマイクロカプセルの含有量は、本発明のマイクロカプセルの効果を十分に発揮させる観点から、0.1〜20重量%が好ましく、0.2〜10重量%がより好ましい。 The content of the microcapsules in the composition of the present invention is not particularly limited, and can be variously changed depending on its use. When the composition of the present invention is used as a fiber treatment agent composition such as a cleaning composition or a softener composition, the content of the microcapsule of the present invention in the composition is sufficient for the effect of the microcapsule of the present invention. From the viewpoint of exhibiting, 0.1 to 20% by weight is preferable, and 0.2 to 10% by weight is more preferable.
実施例1:ゲラニオールケイ酸エステル含有マイクロカプセルの調製
工程1:ゲラニオールケイ酸エステルの調製
フラスコにテトラエトキシシランとエトキシ基に対して90モル%のゲラニオールとゲラニオールに対して0.044モル%のKOH(エタノール溶液)を仕込み、窒素置換した。次に120℃で2時間反応させた後に10.6 kPaに減圧し、4時間熟成することにより、テトラ(ゲラニルオキシ)シランを含むゲラニオールケイ酸エステルを得た。
Example 1: Preparation of Geraniol Silicate-Containing Microcapsules Step 1: Preparation of Geraniol Silicate Ester In a flask, 90 mol% geraniol with respect to tetraethoxysilane and ethoxy groups and 0.044 mol% KOH (ethanol with respect to geraniol) Solution) was charged and the atmosphere was replaced with nitrogen. Next, after reacting at 120 ° C. for 2 hours, the pressure was reduced to 10.6 kPa and aging was performed for 4 hours to obtain geraniol silicate ester containing tetra (geranyloxy) silane.
工程2:マイクロカプセルの調製
15重量部のエチレン−無水マレイン酸共重合体(Scripset-520、モンサント製)と水85重量部を加え60℃で混合し、pHを4に調整することにより乳化剤Aを得た。
Step 2: Preparation of microcapsules
Emulsifier A was obtained by adding 15 parts by weight of ethylene-maleic anhydride copolymer (Scripset-520, manufactured by Monsanto) and 85 parts by weight of water, mixing at 60 ° C., and adjusting the pH to 4.
また、メラミン−ホルムアルデヒド樹脂(商品名Sumirez Resin 615K、住友化学製)15重量部に水85重量部を加え60℃で混合することにより壁材Bを得た。 Further, wall material B was obtained by adding 85 parts by weight of water to 15 parts by weight of melamine-formaldehyde resin (trade name Sumirez Resin 615K, manufactured by Sumitomo Chemical Co., Ltd.) and mixing at 60 ° C.
100重量部の乳化剤Aと工程1で調製したゲラニオールケイ酸エステル100重量部を60℃でホモミキサーを用いて乳化した。次に50重量部の壁材Bをこの乳化物に加え、更に2時間攪拌することにより平均粒子径3μm、固形分約40%のゲラニオールケイ酸エステル含有マイクロカプセルスラリーを得た。 100 parts by weight of emulsifier A and 100 parts by weight of geraniol silicate prepared in Step 1 were emulsified at 60 ° C. using a homomixer. Next, 50 parts by weight of the wall material B was added to the emulsion and further stirred for 2 hours to obtain a geraniol silicate-containing microcapsule slurry having an average particle size of 3 μm and a solid content of about 40%.
実施例2:フェニルエチルアルコールケイ酸エステル含有マイクロカプセルの調製
工程1:フェニルエチルアルコールケイ酸エステルの調製
フラスコにデシルトリエトキシシランとエトキシ基に対して95モル%のフェニルエチルアルコールとフェニルエチルアルコールに対して0.044モル%のNaOCH3を仕込み、窒素置換した。次に120℃で2時間反応させた後に10.6 kPaに減圧し、4時間熟成することにより、トリス(フェニルエチルオキシ)デシルシランを含むフェニルエチルアルコールケイ酸エステルを得た。
Example 2: Preparation of Phenylethyl Alcohol Silicate-Containing Microcapsules Step 1: Preparation of Phenylethyl Alcohol Silicate Ester In a flask, 95 mol% phenylethyl alcohol and phenylethyl alcohol based on decyltriethoxysilane and ethoxy groups On the other hand, 0.044 mol% of NaOCH 3 was charged and purged with nitrogen. Next, after reacting at 120 ° C. for 2 hours, the pressure was reduced to 10.6 kPa and aging was performed for 4 hours to obtain phenylethyl alcohol silicate ester containing tris (phenylethyloxy) decylsilane.
工程2:マイクロカプセルの調製
ゲラニオールケイ酸エステルの代わりに、工程1で調製したフェニルエチルアルコールケイ酸エステルを用いる以外は実施例1の工程2と同様にして、平均粒子径2μm、固形分約40%のフェニルエチルアルコールケイ酸エステル含有マイクロカプセルスラリーを得た。
Step 2: Preparation of microcapsules An average particle size of 2 μm and a solid content of about 40 were obtained in the same manner as in Step 2 of Example 1, except that phenylethyl alcohol silicate prepared in Step 1 was used instead of geraniol silicate. % Phenylethyl alcohol silicate-containing microcapsule slurry was obtained.
実施例3:アニスアルコールケイ酸エステル含有マイクロカプセルの調製
工程1:アニスアルコールケイ酸エステルの調製
フラスコに1,3,5,7,9−ペンタエトキシ−1,3,5,7,9−ペンタメチルシクロペンタシロキサンとエトキシ基に対して120モル%のアニスアルコールとアニスアルコールに対して0.044モル%のNaOCH2CH3を仕込み、窒素置換した。次に120℃で2時間反応させた後に10.6 kPaに減圧し、6時間熟成することにより、1,3,5,7,9−ペンタ(アニスアルコキシ)−1,3,5,7,9−ペンタメチルシクロペンタシロキサンを含むアニスアルコールケイ酸エステルを得た。
Example 3: Preparation of anis alcohol silicate-containing microcapsules Step 1: Preparation of anis alcohol silicate 1,3,5,7,9-pentaethoxy-1,3,5,7,9-penta in a flask 120 mol% of anis alcohol and 0.044 mol% of NaOCH 2 CH 3 based on methyl cyclopentasiloxane and ethoxy groups were charged with nitrogen. Next, after reacting at 120 ° C. for 2 hours, reducing the pressure to 10.6 kPa and aging for 6 hours, 1,3,5,7,9-penta (anisalkoxy) -1,3,5,7,9- Anis alcohol silicate ester containing pentamethylcyclopentasiloxane was obtained.
工程2:マイクロカプセルの調製
尿素10重量部に、レゾルシン2重量部と3重量部のエチレン−無水マレイン酸共重合体(Scripset-520、モンサント製)と85重量部の水を混合し、pHを3に調整することにより壁材・乳化剤混合物Cを得た。
Step 2: Preparation of microcapsules 10 parts by weight of urea is mixed with 2 parts by weight of resorcin and 3 parts by weight of ethylene-maleic anhydride copolymer (Scripset-520, manufactured by Monsanto) and 85 parts by weight of water, and the pH is adjusted. The wall material / emulsifier mixture C was obtained by adjusting to 3.
得られた壁材・乳化剤混合物C 50重量部と工程1で調製したアニスアルコールケイ酸エステル40重量部を60℃でホモミキサーを用いて乳化した。次に10重量部のホルムアルデヒドをこの乳化物に加え、更に2時間攪拌することにより平均粒子径3μm、固形分約40%のアニスアルコールケイ酸エステル含有マイクロカプセルスラリーを得た。 50 parts by weight of the obtained wall material / emulsifier mixture C and 40 parts by weight of anise alcohol silicate ester prepared in Step 1 were emulsified at 60 ° C. using a homomixer. Next, 10 parts by weight of formaldehyde was added to this emulsion and further stirred for 2 hours to obtain an anis alcohol silicate-containing microcapsule slurry having an average particle size of 3 μm and a solid content of about 40%.
比較例1
実施例2の工程1で調製したフェニルエチルアルコールケイ酸エステルに代えて、フェニルエチルアルコールを用い、実施例2の工程2と同様の方法でカプセル化を試みた。しかしながら、壁材を加えた際に乳化状態が不良となり、フェニルエチルアルコール含有マイクロカプセルを得ることが出来なかった。
Comparative Example 1
In place of the phenylethyl alcohol silicate prepared in Step 1 of Example 2, phenylethyl alcohol was used, and encapsulation was attempted in the same manner as in Step 2 of Example 2. However, when the wall material was added, the emulsified state was poor, and phenylethyl alcohol-containing microcapsules could not be obtained.
比較例2
15重量部のエチレン−無水マレイン酸共重合体(Scripset-520、モンサント製)と水85重量部を加え60℃で混合し、pHを4に調整することにより、乳化剤Aを得た。
Comparative Example 2
Emulsifier A was obtained by adding 15 parts by weight of ethylene-maleic anhydride copolymer (Scripset-520, manufactured by Monsanto) and 85 parts by weight of water, mixing at 60 ° C., and adjusting the pH to 4.
また、メラミン−ホルムアルデヒド樹脂(商品名Sumirez Resin 615K、住友化学製)15重量部に水85重量部を加え60℃で混合することにより壁材Bを得た。 Further, wall material B was obtained by adding 85 parts by weight of water to 15 parts by weight of melamine-formaldehyde resin (trade name Sumirez Resin 615K, manufactured by Sumitomo Chemical Co., Ltd.) and mixing at 60 ° C.
100重量部の乳化剤Aとゲラニオール100重量部を60℃でホモミキサーを用いて乳化した。次に50重量部の壁材Bをこの乳化物に加え、更に2時間攪拌することにより平均粒子径3μm、固形分約40%のゲラニオール含有マイクロカプセルスラリーを得た。 100 parts by weight of emulsifier A and 100 parts by weight of geraniol were emulsified at 60 ° C. using a homomixer. Next, 50 parts by weight of the wall material B was added to this emulsion and further stirred for 2 hours to obtain a geraniol-containing microcapsule slurry having an average particle size of 3 μm and a solid content of about 40%.
比較例3
フラスコにテトラエトキシシランとエトキシ基に対して90モル%のフェニルエチルアルコールとフェニルエチルアルコールに対して0.044モル%のKOH(エタノール溶液)を仕込み、窒素置換した。次に120℃で2時間反応させた後に10.6 kPaに減圧し、4時間熟成することにより、テトラ(フェニルエチルオキシ)シランを含むフェニルエチルアルコールケイ酸エステルを得た。
Comparative Example 3
The flask was charged with tetraethoxysilane, 90 mol% of phenylethyl alcohol with respect to the ethoxy group, and 0.044 mol% of KOH (ethanol solution) with respect to phenylethyl alcohol, and purged with nitrogen. Next, after reacting at 120 ° C. for 2 hours, the pressure was reduced to 10.6 kPa and aging was performed for 4 hours to obtain phenylethyl alcohol silicate ester containing tetra (phenylethyloxy) silane.
実施例1〜3及び比較例2で得られたケイ酸エステル含有マイクロカプセル又は比較例3で得られたケイ酸エステルを用い、下記方法に従って衣料用柔軟剤を調製し、柔軟処理を行い、香りの持続性(残香性)を評価した。結果を表1に示す。 Using the silicate ester-containing microcapsules obtained in Examples 1 to 3 and Comparative Example 2 or the silicate ester obtained in Comparative Example 3, a fabric softener was prepared according to the following method, subjected to a softening treatment, and a fragrance. The sustainability (residual scent) was evaluated. The results are shown in Table 1.
<衣料用柔軟剤組成物の調製法>
攪拌器とジムロート冷却器のついた500mL四つ口フラスコにイオン交換水229.86gを仕込み、500rpmで攪拌しながらマントルヒーターで62℃まで昇温し、融解したTETRANYL L1/90S(Kao Corporation, S.A.製)13.89gを添加した。次に実施例1〜3及び比較例2で調製したマイクロカプセルスラリー6.25g、あるいは比較例3で調製したケイ酸エステル2.5gと水3.75gを添加し、5分間攪拌した後、5℃のウォーターバスで30℃まで冷却し、衣料用柔軟剤組成物を得た。
<Method for preparing softener composition for clothing>
A 500 mL four-necked flask equipped with a stirrer and a Dimroth condenser was charged with 229.86 g of ion-exchanged water, heated to 62 ° C with a mantle heater while stirring at 500 rpm, and melted TETRANYL L1 / 90S (manufactured by Kao Corporation, SA) ) 13.89 g was added. Next, 6.25 g of the microcapsule slurry prepared in Examples 1 to 3 and Comparative Example 2 or 2.5 g of the silicate ester prepared in Comparative Example 3 and 3.75 g of water were added and stirred for 5 minutes, followed by 5 ° C. water. The bath was cooled to 30 ° C. to obtain a softener composition for clothing.
<衣料用柔軟剤組成物による繊維製品の処理と残香性評価>
(1) 前処理
あらかじめ、市販の弱アルカリ性洗剤(花王(株)アタック)を用いて、木綿タオル24枚を日立全自動洗濯機NW-6CYで5回洗浄を繰り返し、室内乾燥することによって、過分の薬剤を除去した(洗剤濃度0.0667重量%、水道水47L使用、水温20℃、洗浄10分、ため濯ぎ2回)。
<Treatment of textile products and evaluation of residual fragrance by softener composition for clothing>
(1) Pretreatment Using a commercially available weak alkaline detergent (Kao Attack), 24 cotton towels were washed 5 times with Hitachi fully automatic washing machine NW-6CY and dried indoors. Were removed (detergent concentration 0.0667% by weight, using 47 L of tap water, water temperature 20 ° C., washing 10 minutes, twice for rinsing).
(2) 繊維製品の処理
National 電気バケツN-BK2-Aに、5Lの水道水を注水し、衣料用柔軟剤組成物を15g/衣料1.0kgとなるように分散させ、上述の方法で前処理を行った2枚の木綿タオルを5分間浸漬した後に、処理タオルを日立全自動洗濯機に加えて3分間脱水を行ってから、24時間乾燥した。
(2) Processing of textile products
Two pieces of cotton that were pretreated by the above method by pouring 5L of tap water into National Electric Bucket N-BK2-A and dispersing the softener composition for clothing to 15g / 1.0kg of clothing. After soaking the towel for 5 minutes, the treated towel was added to the Hitachi fully automatic washing machine, dehydrated for 3 minutes, and then dried for 24 hours.
(3) 残香性評価
上述の方法で処理乾燥したタオルを手で揉んで室内に放置し、乾燥・手揉み直後、3日後、1週間後、2週間後、4週間後の香りを香り強度専門パネラー10人により下記基準で官能評価し、平均値を求めた。
(3) Residual odor evaluation The towels treated and dried by the above-mentioned method are rubbed by hand and left in the room. After drying / hand-rubbing, the scents after 3 days, 1 week, 2 weeks, and 4 weeks are specialized. Sensory evaluation was performed by 10 panelists according to the following criteria, and an average value was obtained.
残香性の評価基準
3:用いた香料の強い香りがする。
2:用いた香料の香りが判別できる。
1:用いた香料の香りとは判別できないが、何か香りがする。
0:香りが無い
Evaluation criteria for residual fragrance 3: The fragrance used has a strong scent.
2: The fragrance of the used fragrance can be identified.
1: Although it cannot be distinguished from the fragrance of the used fragrance, it smells something.
0: No scent
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