CN113766969A - 用于制备微胶囊的方法 - Google Patents
用于制备微胶囊的方法 Download PDFInfo
- Publication number
- CN113766969A CN113766969A CN201980095136.6A CN201980095136A CN113766969A CN 113766969 A CN113766969 A CN 113766969A CN 201980095136 A CN201980095136 A CN 201980095136A CN 113766969 A CN113766969 A CN 113766969A
- Authority
- CN
- China
- Prior art keywords
- microcapsules
- oil
- methyl
- acetate
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 157
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 75
- 230000008569 process Effects 0.000 claims abstract description 56
- 239000012948 isocyanate Substances 0.000 claims abstract description 54
- 239000004480 active ingredient Substances 0.000 claims abstract description 53
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 52
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 42
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 239000000725 suspension Substances 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000003599 detergent Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000003623 enhancer Substances 0.000 claims abstract description 11
- 239000002979 fabric softener Substances 0.000 claims abstract description 6
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
- 229940127557 pharmaceutical product Drugs 0.000 claims abstract description 5
- 239000002775 capsule Substances 0.000 claims description 85
- -1 cycloaliphatic Chemical group 0.000 claims description 63
- 239000008346 aqueous phase Substances 0.000 claims description 61
- 239000003205 fragrance Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 40
- 239000000084 colloidal system Substances 0.000 claims description 37
- 238000004132 cross linking Methods 0.000 claims description 36
- 230000001681 protective effect Effects 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 33
- 230000002209 hydrophobic effect Effects 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 26
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- 230000002378 acidificating effect Effects 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 18
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003995 emulsifying agent Substances 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 11
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229920000881 Modified starch Polymers 0.000 claims description 9
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 9
- 235000019426 modified starch Nutrition 0.000 claims description 9
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical group C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims description 8
- 229920002396 Polyurea Polymers 0.000 claims description 8
- 229920001228 polyisocyanate Polymers 0.000 claims description 8
- 239000005056 polyisocyanate Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000004368 Modified starch Substances 0.000 claims description 7
- 229920002472 Starch Polymers 0.000 claims description 7
- 150000002540 isothiocyanates Chemical class 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- 235000019698 starch Nutrition 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 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
- 239000008107 starch Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000007046 ethoxylation reaction Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
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- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 4
- 235000013824 polyphenols Nutrition 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
- 239000003905 agrochemical Substances 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
- 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 class Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-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
- 229940083957 1,2-butanediol Drugs 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
- 229940035437 1,3-propanediol Drugs 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class 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
- 150000004985 diamines Chemical class 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
- 229940093476 ethylene glycol Drugs 0.000 claims description 2
- 235000013373 food additive Nutrition 0.000 claims description 2
- 239000002778 food additive Substances 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
- 239000002917 insecticide 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
- 230000003287 optical effect Effects 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
- 239000000049 pigment Substances 0.000 claims description 2
- 229920000768 polyamine Polymers 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
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000004072 triols Chemical class 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 239000011162 core material Substances 0.000 abstract description 27
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 5
- 239000003921 oil Substances 0.000 description 109
- 235000019198 oils Nutrition 0.000 description 109
- 239000011257 shell material Substances 0.000 description 35
- 239000002304 perfume Substances 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 24
- 239000000463 material Substances 0.000 description 24
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- 239000002245 particle Substances 0.000 description 19
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 17
- 238000005538 encapsulation Methods 0.000 description 15
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- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 13
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
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- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 238000004945 emulsification Methods 0.000 description 10
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 10
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 10
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 9
- 235000019645 odor Nutrition 0.000 description 9
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- 239000004857 Balsam Substances 0.000 description 8
- 244000018716 Impatiens biflora Species 0.000 description 8
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 8
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 description 8
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer 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
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 8
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- 238000009826 distribution Methods 0.000 description 7
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- JIMGVOCOYZFDKB-UHFFFAOYSA-N 2-phenylethyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OCCC1=CC=CC=C1 JIMGVOCOYZFDKB-UHFFFAOYSA-N 0.000 description 6
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Abstract
本发明涉及一种用于制备微胶囊的方法,尤其用于制备基于异氰酸酯的微胶囊的方法,所述微胶囊针对作为芯材料的包含羧酸和醛的有效成分具有改进的稳定性。此外,本发明涉及可以根据本发明方法获得的微胶囊。另外,本发明涉及微胶囊、此类微胶囊的悬浮液以及所述微胶囊和悬浮液用作洗涤剂、织物柔软剂、清洁剂、呈液态或固态形式的气味增强剂、美妆用品、个人护理产品、农业产品或制药产品的组成部分的用途。
Description
技术领域
本发明涉及一种用于制备微胶囊的方法,尤其用于制备基于异氰酸酯的微胶囊的方法,所述微胶囊针对作为芯材料的包含羧酸、醛和/或酯的有效成分具有改进的稳定性。此外,本发明涉及可以根据本发明方法获得的微胶囊。另外,本发明涉及微胶囊、此类微胶囊的悬浮液以及所述微胶囊和悬浮液用作洗涤剂、织物柔软剂、清洁剂、呈液态或固态形式的气味增强剂(香味增强剂)、美妆用品、个人护理产品、农业产品和制药产品的组成部分的用途。
背景技术
本领域技术人员一般将术语“封装”理解为如下的技术:利用所述技术,用由聚合物型或无机物型壁材料形成的成膜壳来包围并由此固定细分散的固态、液态或气态物质。在制备时,聚合物在乳化和凝聚或者界面聚合之后沉积在待封入的物质上。因此封装是一种形式的嵌入固定。被封闭在胶囊内的物质或有效成分通常称为芯材料。
在此的目标是保护被称为有效成分的活性组分并且可以在某一时间点进行针对性的释放。由于不同原因(例如由于其溶解度、反应活性、稳定性等),有效成分或活性组分通常不能直接释放,或者应通过微封装来实现某些效果(例如为了受控释放的释放曲线、独有特征等)。
在>100μm的范围内的直径下,以不同的喷涂工艺来涂覆各个物质颗粒或有效成分颗粒,相反,液体通过液滴化方法来封装。
具有特别意义的是具有在约0.0001至5、优选0.001至0.5以及尤其0.005至0.1mm范围内直径的所谓微胶囊。
然而,对于具有低于100μm直径的微胶囊而言,封装只能通过将所谓的壁形成剂沉积在相界面处来实现。在工业上用于此目的的制备方法中,产生了水包疏水的芯材料的乳液或悬浮液。位于外部相中的单体累积在围绕乳液液滴或者经分散的芯材料固体颗粒的层中并且聚合成紧实的罩壳。于是,依据壁材料和交联度不同,可以实现微胶囊的个体特性。
在封装时有以下区别:基质封装:在此将有效成分或活性组分与壳组分(“基质”)均匀共混并且产生颗粒,在所述颗粒中有效成分或活性组分均匀分布。释放通常由活性组分向环境中的扩散或者由基质的降解速度决定。芯壳封装:用壳材料来包裹构成芯的有效成分或活性组分。产生了具有一个或多个壳的实际的胶囊。壳的破坏一般造成在短时间内完全释放芯材料。但是还可能通过适当选择壳来产生极为缓慢的释放。
由于其特性,微胶囊尤其用在印刷工业、食品工业(维生素、风味剂、植物提取物、酶、微生物)、农业化学(肥料、植物保护剂)、饲料工业(矿物质、维生素、酶、药剂、微生物)、制药工业、清洗剂工业以及美妆工业。
可以出于多种原因来用适当的壁材料(涂覆材料)封装有效成分:
-将液体转化为可处理的粉末形式(例如植物油、脂肪的涂层);
-在时间上受控地释放物质(在药剂、植物保护剂和肥料情况下的剂量控制、储存效应);
-味道、气味和颜色的堆叠(例如更苦的或更辣的芳香物质);
-抵御光、氧化、热、酸或碱(例如维生素、芳香物质等)
-抵御湿气(例如吸湿的盐或矿物质);
-延迟挥发性组分(例如芳香物质)的损失;
-防止与其他混合物组分提前进行化学反应;
-在加工前或期间更好地进行处理(流动特性、粉尘形成);
-保护人员免受对健康有害的或不舒适的材料(化学品、芳香浓缩物);或者
-通过表面改性获得更好的溶解性/可悬浮性。
微胶囊的内容物可以以各种方式释放。在此考虑四种典型的机制:
-通过压碎或剪切来机械地破坏胶囊。这种机制例如用在反应性无碳书写纸(Reaktionsdurchschreibepapier)中。
-通过壁材料的熔化来破坏胶囊。根据这种机制,例如在烘烤混合物中,只有在烘烤过程期间才释放内容物(如膨松剂或风味剂)。
-通过壁材料的溶解来破坏胶囊。这种机制例如在洗衣粉的情况下起作用,由此只有在清洗过程时才释放被封装的内容物质(如酶)。
-胶囊保持不变,胶囊内容物通过扩散逐渐穿过胶囊壁而得以释放。根据这种机制,例如可以实现在体内缓慢且均匀地释放药剂有效成分。
现在,日常需求的许多物品,例如清洁剂、柔软剂、洗衣粉、洗衣液、沐浴露、洗发水、除臭剂、多重浴液(Polylotionen)等,都用香味剂或香味剂混合物来增香。这非常常见地造成香味剂与配方的其他组成部分的相互作用,或者造成增香剂的较易挥发组分的提前蒸发。这一般导致增香剂的气味印象随时间流逝而变化或者甚至完全消失。
此类香味剂混合物的微封装提供了如下可能性:减少或完全防止经增香产品中的相互作用或易挥发组分的蒸发。
化学上和机械上都稳定的微胶囊例如基于用作壁材料或壳材料的氨基塑料树脂。除了胶囊壳的高密封性之外,胶囊壳针对反应性化学品也有非常高的耐受性。以如下方式简化这种胶囊的制备:首先在强剪切下并且在乳化剂存在下制备O/W乳液,所述乳液包含溶于水的单体,即所谓的胺-甲醛预缩合物,和不溶于水的疏水有效成分,如香水油。预缩聚通过改变pH值来引发,例如通过加入酸将pH值调节到约3.5。缩聚物沉积在乳液中的小油滴上并且逐渐将其包裹。在缩聚结束之后由乳液产生微胶囊分散体。然而胶囊仍然拥有软的、弹性的壳,所述壳尚未提供所需的扩散稳定性和材质特性。因此随后是另一个步骤,其中将微胶囊分散体的温度升高到约60℃,这造成壁部中聚合物的交联以及胶囊的硬化。对应的方法例如是从EP 2 111 214 B1(GIVAUDAN)中已知的。
从DE 23 03 866 A1(FUJI)已知一种用于制备微胶囊的稳定的经浓缩的混合物,所述混合物包含(a)环氧丙基三烷基铵盐并且另外包含磺基琥珀酸烷基酯或者磺基琥珀酰胺酸烷基酯,所述磺基琥珀酸烷基酯具有带有6至16个碳原子的烷基,所述磺基琥珀酰胺酸烷基酯的羧酸酰胺基团被带有8至20个碳原子的烷基取代,并且所述混合物包含可与水混合的溶剂作为组分(b)。
EP 2 669 835 A1(KOEHLER)的主题是一种用于制备微胶囊的方法。这些微胶囊的特征是具有至少两个最大值的特殊的粒径分布,其中粒径的主最大值在5至100μm的范围内并且其中粒径小于或等于主最大值粒径四分之一的微胶囊所占有的体积大于或等于微胶囊的总体积的约20%。胶囊壁部在此可以由甲基化的三聚氰胺-甲醛树脂和/或脲-甲醛树脂和/或醛与硫脲、N-烷基脲、胍、乙酰胍胺、苯并胍胺、癸酰胍胺(Caprionoguanamin)、氰胺、二氰二胺和/或烷基/芳基磺酰胺的反应产物组成。
EP 3 238 816 A1(SYMRISE)公开了一种用于制备微胶囊、尤其氨基塑料微胶囊的方法,其中预聚物水相和包含待封装的有效成分的非水相的乳化在至少一种1,2-二醇的存在下进行,这实现了微胶囊粒径的明显减小并由此产生了乳液的稳定化。
WO 2017/148504(SYMRISE)涉及一种用于制备香味剂胶囊的方法,其中用天然的覆盖材料或合成的阴离子型或阳离子型聚合物或其混合物来封装就在封装之前具有最大5mg KOH/g的酸度值的香味剂组合物。
此外,微胶囊可以由丙烯酸单体、聚脲或还有生物聚合物如明胶和其他蛋白质或无机壁材料制备。在根据现有技术制备的基于异氰酸酯的微胶囊中,多异氰酸酯与碳酸胍作为交联剂在碱性环境中反应。
与氨基塑料树脂相比,用异氰酸酯封装的优点是微胶囊不含甲醛。然而,用异氰酸酯和其他壁材料封装的缺点是,由此只能封装有限量的有效成分(例如香味物质或香味油)并提供稳定的微胶囊。用异氰酸酯和其他壁材料的封装尤其不适合于封装具有醛、羧酸或酯官能度的香味物质或香味油。即,当在碱性pH值下封装时,羧酸被去质子化,氧化的醛(羧酸)类似,而酯被皂化,从而使所获得的乳液变得不稳定。由此,此类微封装的使用在有效成分方面是受限的并且因此例如仅适合用于小范围的香味物质或香味油,而对于具有醛、羧酸或酯官能度的香味物质或香味油,此类微封装被排除在外。然而,具有醛、羧酸或酯官能度的香味剂恰恰属于香味物质或香味油的最重要的代表物。
在此背景下,本发明以如下复杂的目的为基础,即提供一种用于制备微胶囊的方法,所述方法一方面能够实现无甲醛的、在待封装的有效成分方面有广泛可变性(尤其具有醛、羧酸或酯官能度的有效成分)的封装,并且另一方面产生了储存稳定且具有出色的有效成分释放行为的微胶囊。
出人意料地已经发现,这个目的可以通过以下方式实现:在水性乳液中在保护胶体和催化剂存在下通过两个彼此相继的交联步骤在不同pH值下分别用胺来制备主要由异氰酸酯构成的胶囊壳或胶囊壁通过在从酸向碱的pH梯度下的两步式交联,可以形成多层的胶囊壳或胶囊壁,由此本身可以封装具有醛、羧酸或酯官能度的有效成分(例如香味剂)。
在方法技术方面的优点在于,通过用第一交联剂在酸性pH值下的交联,待封装的有效成分的官能团,在通过加入另一种碱性交联剂来提高pH值之前,被第一聚合物层来保护。
发明内容
本发明的第一个主题因此涉及一种用于制备基于异氰酸酯的微胶囊的方法,所述方法包括以下步骤或由以下步骤组成:
(a)提供内部的非水相,所述非水相包括至少一种带有两个或更多个异氰酸酯基团的异氰酸酯或者至少一种带有两个或更多个异硫氰酸酯基团的异硫氰酸酯以及待封装的疏水有效成分;
(b)提供外部的水相,所述水相包括至少一种保护胶体和催化剂;
(c)任选地在稳定剂和/或乳化剂的存在下,将所述内部的非水相和所述外部的水相混合,获得水包油乳液;
(d)通过添加在酸性pH值下反应的胺进行第一交联;
(e)通过添加在碱性pH值下反应的胺进行进一步交联,获得微胶囊;
(f)将在步骤(e)中获得的微胶囊硬化;以及
任选地
(g)将所述微胶囊与反应溶液分离并且任选地干燥所述微胶囊。
此外,本发明的主题为根据本发明方法制备的微胶囊。
本发明的另一个方面是微胶囊,所述微胶囊包括以下项或由以下项组成:
-芯,所述芯包括至少一种疏水的有效成分或由其组成;以及
-胶囊壳,所述胶囊壳包括具有至少两个或更多个异氰酸酯基团的异氰酸酯,所述异氰酸酯在保护胶体和催化剂的存在下在第一步骤中通过在酸性pH值下反应的胺并且在另外的步骤中通过在碱性pH值下反应的胺进行交联。
最后,在另一个方面,本发明涉及本发明的微胶囊或包括本发明微胶囊的悬浮液用于制备洗涤剂、织物柔软剂、清洁剂、气味增强剂(香味增强剂)、美妆用品、身体清洁产品、农业产品或制药产品的用途。
对于本领域技术人员而言,本发明的这些和其他方面、特征和优点可以从对以下详细说明和权利要求书的学习中得出。在此,来自本发明一方面的任何特征可以用在本发明的另一方面中或者进行交换。此外,不言而喻的是,本文中包含的实施例描述并且展示本发明,但是这些实施例不应限制本发明,并且本发明尤其不限于这些实施例。
如果没有另外提及,所有的百分比数值都是重量%。以“从x到y”的形式给出的数值的例子包括所提及的值。当然,当以此格式给出多个优选的数值范围时,同样记载了由不同端点的组合产生的所有范围。
附图说明
图1是放大10倍的本发明微胶囊的光学显微镜照片。使用Olympus BX51进行光学显微镜拍摄。
图2是关于具有不同香水油的本发明微胶囊的粒径分布(d(0.5)值)的图表。
图3是关于具有不同香水油的来自现有技术的微胶囊的粒径分布(d(0.5)值)的图表。
图4是关于具有香水油4或5的本发明微胶囊的Zeta电位的图表。
图5是关于具有香水油1或2的来自现有技术的微胶囊的Zeta电位的图表。
图6是示出来自现有技术的微胶囊和本发明微胶囊的感受评估结果的图表。
具体实施方式
在第一方面,本发明涉及一种用于制备基于异氰酸酯的微胶囊的方法,所述方法包括以下步骤或由以下步骤组成:
(a)提供内部的非水相,所述非水相包括至少一种带有两个或更多个异氰酸酯基团的异氰酸酯或者至少一种带有两个或更多个异硫氰酸酯基团的异硫氰酸酯以及待封装的疏水有效成分;
(b)提供外部的水相,所述水相包括至少一种保护胶体和催化剂;
(c)任选地在稳定剂和/或乳化剂的存在下,将所述内部的非水相和所述外部的水相混合,获得水包油乳液;
(d)通过添加在酸性pH值下反应的胺进行第一交联;
(e)通过添加在碱性pH值下反应的胺进行进一步交联,获得微胶囊;
(f)将在步骤(e)中获得的微胶囊硬化;以及
任选地
(g)将所述微胶囊从反应溶液中分离并且任选地干燥所述微胶囊。
在本发明的上下文中,微胶囊理解为具有胶囊壳或胶囊壁以及在胶囊内部中作为芯材料的一种或多种疏水有效成分的微颗粒。
在本发明方法的第一步骤中提供了内部的非水相,该非水相包括至少一种具有至少两个或更多个异氰酸酯基团的异氰酸酯以及待封装的疏水的有效成分。
可根据本发明使用的能够聚合以形成胶囊壳或胶囊壁的异氰酸酯化合物或异氰酸酯单体为具有至少两个、三个、四个或更高官能度的异氰酸酯基团或异硫氰酸酯基团的那些异氰酸酯或异硫氰酸酯,尤其为脂肪族、环脂肪族、氢化芳香族、芳香族或杂环的多异氰酸酯或多异硫氰酸酯、其取代产物以及上述化合物的混合物。多异氰酸酯优选为二异氰酸酯。仍更优选的是芳香族的二异氰酸酯。
通过使用包含至少两个异氰酸酯或异硫氰酸酯基团的能够聚合的不同化合物,还可以制备混合聚合产物。
可根据本发明使用的包含至少两个异氰酸酯或至少两个异硫氰酸酯基团的单体的例子为:亚乙基二异氰酸酯,三亚甲基二异氰酸酯,1,4-四亚甲基二异氰酸酯,1,6-六甲基二异氰酸酯,亚乙基二异硫氰酸酯,四亚甲基二异硫氰酸酯,六亚甲基二异硫氰酸酯,环丁烷-1,3-二异氰酸酯,环己烷-1,3-二异氰酸酯,环己烷-1,4-二异氰酸酯,1,3-亚苯基二异氰酸酯,1,4-亚苯基二异氰酸酯,1,3-亚苯基二异氰酸酯和1,4-亚苯基二异氰酸酯的混合物,对亚苯基二异硫氰酸酯,亚二甲苯基-1,4-二异硫氰酸酯,2,4-亚甲苯基二异氰酸酯,2,6-亚甲苯基二异氰酸酯,2,4-亚甲苯基二异氰酸酯和2,6-亚甲苯基二异氰酸酯的混合物,亚二甲苯基-1,4-二异氰酸酯,亚二甲苯基-1,3-二异氰酸酯,以及亚二甲苯基-1,4-二异氰酸酯和亚二甲苯基-1,3-二异氰酸酯的混合物,2,4-六氢亚甲苯基二异氰酸酯,2,6-六氢亚甲苯基二异氰酸酯,2,4-六氢亚甲苯基二异氰酸酯和2,6-六氢亚甲苯基二异氰酸酯的混合物,六氢-1,3-亚苯基二异氰酸酯,六氢-1,4-亚苯基二异氰酸酯,六氢-1,4-亚苯基二异氰酸酯和六氢-1,4-亚苯基二异氰酸酯的混合物,1,3-二异氰酸酯基苯,1,3,5-三甲基苯-2,4-二异氰酸酯,1,3,5-三异丙基苯-2,4-二异氰酸酯,二苯基甲烷-4,4'-二异氰酸酯,3,3'-二甲基二苯基甲烷-4,4'-二异氰酸酯,4,4'-二苯基丙烷二异氰酸酯,亚萘基-1,4-二异氰酸酯,亚萘基-1,5-二异氰酸酯,三苯基甲烷-4,4',4"-三异氰酸酯,甲苯-2,4,6-三异氰酸酯(Toluylen-2,4,6-triisocyanat),二甲基二苯基甲烷-2,2',5,5'-四异氰酸酯或上述化合物的混合物。
作为具有至少两个异氰酸酯基团或异硫氰酸酯基团的能够聚合的化合物优选的是大规模制备的二异氰酸酯和多异氰酸酯,例如TDI亚甲苯基二异氰酸酯(2,4-和2,6-亚甲苯基二异氰酸酯以80:20的比的异构体混合物),HDI六亚甲基二异氰酸酯-(1,6),IPDI异佛尔酮二异氰酸酯或DMDI二苯基甲烷-4,4'-二异氰酸酯。
在本发明方法中可以使用的其他的初始异氰酸酯为:二异氰酸酯,如1,4-二异氰酸酯基丁烷、1,6-二异氰酸酯基己烷、1,5-二异氰酸酯基-2,2-二甲基戊烷、2,2,4-和2,4,4-三甲基-1,6-二异氰酸酯基己烷、1,10-二异氰酸酯基癸烷、1,3-和1,4-二异氰酸酯基环己烷、1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷(异佛尔酮二异氰酸酯)、4,4'-二异氰酸酯基二环己基甲烷、2,4-和2,6-二异氰酸酯基甲基环己烷及其混合物。理论上还可以使用芳香族的异氰酸酯,例如亚甲苯基二异氰酸酯或4,4'-二异氰酸酯基-二苯基甲烷。
部分地还可以同时使用如下多异氰酸酯:所述多异氰酸酯可以通过根据已知方法改性上述二异氰酸酯或其混合物来形成并且例如包含脲二酮、氨基甲酸酯、异氰酸酯、缩二脲和/或脲基甲酸酯基团。
异氰酸酯组分在内部的非水相中的比例为相对于所述非水相的总重量在1至8重量%范围内、优选在3至7重量%范围内。最优选地,异氰酸酯组分以相对于所述非水相的总重量5至6重量%的范围用在内部的非水相中。
作为用于制备本发明微胶囊的芯材料可以考虑任何适合于包封在微胶囊中的材料。作为待封装的材料优选考虑疏水的、不溶于水的或不能与水混合的液体或固体以及悬浮液。在本说明书的上下文中,术语“疏水材料”是指待封装的材料位于内部的非水相中并且不与外部的水相混合。
在一个特别优选的实施方式中,根据本发明的微胶囊被设计为,使其具有由至少一种疏水的有效成分形成的芯材料,尤其疏水的香味物质或疏水的香味油、农药、杀生物剂、杀昆虫剂、选自趋避剂的组的物质、食品添加剂、美妆有效成分、制药有效成分、染料、农业化学品、染料、发光颜料、光学增亮剂、溶剂、蜡、硅酮油、润滑剂,以及上述有效成分的混合物,也就是说只要其足够不溶于水或者与水相不混合,因为否则无法形成乳液并且无法在小液滴表面上产生聚合物沉积。
在本发明第一方面的一个优选变体中,尤其考虑疏水的香味物质或香味油、风味剂或生物源成分作为有效成分。
在一个优选的实施方式中,本发明的微胶囊具有呈疏水的单独香味物质或单独香味剂形式的芯材料,其中所述芯材料包括选自下组中的一项或多项的至少一种单独香味物质或单独香味剂或其混合物:
-烃,例如3-蒈烯;α-蒎烯;β-蒎烯;α-萜烯;γ-萜烯;对伞花烃;红没药醇;莰烯;石竹烯;雪松烯;金合欢烯;柠檬烯;长叶烯;月桂烯;罗勒烯;巴伦西亚桔烯;(E,Z)-1,3,5-十一碳三烯;
-脂肪醇例如己醇;辛醇;3-辛醇;2,6-二甲基庚醇;2-甲基庚醇,2-甲基辛醇;(E)-2-己烯醇;(E)-和(Z)-3-己烯醇;1-辛烯-3-醇;3,4,5,6,6-五甲基-3,4-庚烯-2-醇和3,5,6,6-四甲基-4-亚甲基庚烷-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛烷-2-醇;9-癸烯醇;10-十一碳烯醇;4-甲基-3-癸烯-5-醇;
-脂肪醛及其缩醛,例如己醛;庚醛;辛醛;壬醛;癸醛;十一碳醛;十二碳醛;十三碳醛;2-甲基辛醛;2-甲基壬醛;(E)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一碳烯醛;(E)-4-癸烯醛;2-十二碳烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛二乙缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅基氧基乙醛;
-脂肪酮及其酮肟,例如2-庚酮;2-辛酮;3-辛酮;2-壬酮;5-甲基-3-庚酮;5-甲基-3-庚酮肟;2,4,4,7-四甲基-6-辛烯-3-酮;
-脂肪族含硫化合物,例如3-甲基硫代己醇;3-甲基硫代己基乙酸酯;3-巯基己醇;3-巯基己基乙酸酯;3-巯基己基丁酸酯;3-乙酰基硫代己基乙酸酯;1-薄荷烯-8-硫醇;
-脂肪族腈,例如2-壬烯酸腈;2-十三碳烯酸腈;2.12-十三碳烯酸腈;3,7-二甲基-2,6-辛二烯酸腈;3,7-二甲基-6-辛烯酸腈;
-脂肪族羧酸及其酯,例如(E)-和(Z)-3-己烯醇甲酸酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;3,5,5-三甲基己基乙酸酯;3-甲基-2-丁烯基乙酸酯;(E)-2-己烯基乙酸酯;(E)-和(Z)-3-己烯基乙酸酯;乙酸辛酯;3-辛基乙酸酯;1-辛烯-3-基乙酸酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)-和(Z)-3-己烯醇异丁酸酯;巴豆酸己酯;异戊酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;乙基-(E,Z)-2,4-癸二烯酸酯;2-辛炔酸甲酯;2-壬炔酸甲酯;2-异戊氧基乙酸烯丙酯;甲基-3,7-二甲基-2,6-辛二烯酸酯;
-非环状萜醇,例如香茅醇;香叶醇;橙花醇;芳樟醇;薰衣草醇;橙花叔醇;金合欢醇;四氢芳樟醇;四氢香叶醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛烷-2-醇;2-甲基-6-亚甲基-7-辛烯-2-醇;2,6-二甲基-5,7-辛二烯-2-醇;2,6-二甲基-3,5-辛二烯-2-醇;3,7-二甲基-4,6-辛二烯-3-醇;3,7-二甲基-1,5,7-辛三烯-3-醇;2,6-二甲基-2,5,7-辛三烯-1-醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸酯、3-甲基-2-丁烯酸酯;
-非环状萜醛和萜酮,例如香叶醛;橙花醛;香茅醛;7-羟基-3,7-二甲基辛醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一碳烯醛;香叶基丙酮;以及香叶醛、橙花醛、7-羟基-3,7-二甲基辛醛的二甲基缩醛和二乙基缩醛;
-环状萜醇,例如薄荷醇;异胡薄荷醇;α-萜品醇;萜品醇-4;薄荷烷-8-醇;薄荷烷-1-醇;薄荷烷-7-醇;冰片醇;异冰片醇;芳樟醇氧化物;诺普醇;雪松醇;龙涎醇;香根草醇;愈创醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸酯、3-甲基-2-丁烯酸酯;
-环状萜醛和萜酮,例如薄荷酮;异薄荷酮;8-巯基薄荷烷-3-酮;香芹酮;樟脑;葑酮;α-紫罗兰酮;β-紫罗兰酮;α-正甲基紫罗兰酮;β-正甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-铁;β-铁;α-大马烯酮;β-大马烯酮;γ-大马烯酮;d-大马烯酮;1-(2,4,4-三甲基-2-环己烯-1-基)-2-丁烯-1-酮;1,3,4,6,7,8a-六氢-1,1,5,5-四甲基-2H-2,4a-甲桥萘-8(5H)-酮;诺卡酮;二氢诺卡酮;α-甜橙醛;β-甜橙醛;酰基化的柏木油(甲基柏木基酮);
-环状醇,例如4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异樟脑基环己醇;2,6,9-三甲基-(Z2,Z5,E9)-环十二碳三烯-1-醇;2-异丁基-4-甲基四氢-2H-吡喃-4-醇;来自环脂肪族醇的组,例如3,3,3-三甲基-环己基甲醇;2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇;2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-戊-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇;1-(2,2,6-三甲基环己基)戊-3-醇;1-(2,2,6-三甲基环己基)己-3-醇;
-环状和环脂肪族醚,例如桉叶素;柏木基甲基醚;环十二碳基甲基醚;(乙氧基甲氧基)环十二烷;α-环氧柏木烷;3a,6,6,9a-四甲基十二氢萘并[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基-十二氢萘并[2,1-b]呋喃;1,5,9-三甲基-13-氧杂二环[10.1.0]十三碳-4,8-二烯;玫瑰醚;2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二噁烷;
-环状酮,例如4-叔丁基环己酮;2,2,5-三甲基-5-戊基环戊酮;2-庚基环戊酮;2-戊基环戊酮;2-羟基-3-甲基-2-环戊烯-1-酮;3-甲基-顺式-2-戊烯-1-基-2-环戊烯-1-酮;3-甲基-2-戊基-2-环戊烯-1-酮;3-甲基-4-环十五烯酮;3-甲基-5-环十五烯酮;3-甲基环十五碳酮;4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮;4-叔戊基环己酮;5-环十六烯-1-酮;6,7-二氢-1,1,2,3,3-五甲基-4(5H)-茚酮;9-环十七烯-1-酮;环十五碳酮;环十六碳酮;
-环脂肪族醛,例如2,4-二甲基-3-环己烯甲醛;2-甲基-4-(2,2,6-三甲基-环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
-环脂肪族酮,例如1-(3,3-二甲基环己基)-4-戊烯-1-酮;1-(5,5-二甲基-2-环己烯-1-基)-4-戊烯-1-酮;2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢-2-萘烯基甲基酮;甲基-2,6,10-三甲基-2,5,9-环十二碳三烯基酮;叔丁基-(2,4-二甲基-3-环己烯-1-基)酮;
-环状醇的酯,例如2-叔丁基环己基乙酸酯;4-叔丁基环己基乙酸酯;2-叔戊基环己基乙酸酯;4-叔戊基环己基乙酸酯;十氢-2-萘基乙酸酯;3-戊基四氢-2H-吡喃-4-基乙酸酯;十氢-2,5,5,8a-四甲基-2-萘基乙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5-或-6-茚基乙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5-或-6-茚基丙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5-或-6-茚基异丁酸酯;4,7-甲桥八氢-5-或-6-茚基乙酸酯;
-环脂肪族羧酸的酯,例如烯丙基-3-环己基丙酸酯;烯丙基环己氧基乙酸酯;二氢茉莉酮酸甲酯;茉莉酮酸甲酯;甲基-2-己基-3-氧代环戊烷羧酸酯;乙基-2-乙基-6,6-二甲基-2-环己烯羧酸酯;乙基-2,3,6,6-四甲基-2-环己烯羧酸酯;乙基-2-甲基-1,3-二氧戊环-2-乙酸酯;
-芳香族烃,例如苯乙烯和二苯基甲烷;
-芳香脂肪醇例如苄醇;1-苯基乙基醇;2-苯基乙基醇;3-苯基丙醇;2-苯基丙醇;2-苯氧基乙醇;2,2-二甲基-3-苯基丙醇;2,2-二甲基-3-(3-甲基苯基)丙醇;1,1-二甲基-2-苯基-乙醇;1,1-二甲基-3-苯基丙醇;1-乙基-1-甲基-3-苯基丙醇;2-甲基-5-苯基戊醇;3-甲基-5-苯基戊醇;3-苯基-2-丙烯-1-醇;4-甲氧基苄基醇;1-(4-异丙基苯基)乙醇;
-芳香脂肪族醇与脂肪族羧酸的酯,例如苄基乙酸酯;丙酸苄基酯;异丁酸苄基酯;异戊酸苄基酯;2-苯基乙基乙酸酯;2-苯基乙基丙酸酯;2-苯基乙基异丁酸酯;2-苯基乙基异戊酸酯;1-苯基乙基乙酸酯;α-三氯甲基苄基乙酸酯;α,α-二甲基苯基乙基乙酸酯;α,α-二甲基苯基乙基丁酸酯;乙酸肉桂基酯;2-苯氧基乙基异丁酸酯;4-甲氧基苄基乙酸酯;
-芳香脂肪族醚,例如2-苯基乙基甲基醚;2-苯基乙基异戊基醚;2-苯基乙基-1-乙氧基乙基醚;苯基乙醛二甲基缩醛;苯基乙醛-二乙基缩醛;龙葵醛-二甲基缩醛;苯基乙醛-甘油缩醛;2,4,6-三甲基-4-苯基-1,3-二噁烷;4,4a,5,9b-四氢茚并[1,2-d]-m-二噁英;4,4a,5,9b-四氢-2,4-二甲基茚并[1,2-d]-m-二噁英;
-芳香族和芳香脂肪族醛,例如苯甲醛;苯基乙醛;3-苯基丙醛;氢化阿托醛;4-甲基苯甲醛;4-甲基苯基乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)-丙醛;2-甲基-3-(4-叔丁基苯基)丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛;α-戊基肉桂醛;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧苯甲醛;3,4-二甲氧基苯甲醛;2-甲基-3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧苯基)丙醛;
-芳香族和芳香脂肪族酮,例如苯乙酮;4-甲基苯乙酮;4-甲氧基苯乙酮;4-叔丁基-2,6-二甲基苯乙酮;4-苯基-2-丁酮;4-(4-羟基苯基)-2-丁酮;1-(2-萘基)乙酮;二苯甲酮;1,1,2,3,3,6-六甲基-5-茚满基甲基酮;6-叔丁基-1,1-二甲基-4-茚满基甲基酮;1-[2,3-二氢-1,1,2,6-四甲基-3-(1-甲基乙基)-1H-5-茚基]乙酮;5',6',7',8'-四氢-3',5',5',6',8',8'-六甲基-2-萘乙酮;
-芳香族和芳香脂肪族羧酸及其酯,例如苯甲酸;苯基乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄基酯;甲基苯基乙酸酯;乙基苯基乙酸酯;香叶基苯基乙酸酯;苯基乙基-苯基乙酸酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄基酯;苯基乙基肉桂酸酯;肉桂酸肉桂基酯;烯丙基苯氧基乙酸酯;水杨酸甲酯;异戊基水杨酸酯;水杨酸己酯;水杨酸环己酯;顺式-3-己烯基水杨酸酯;水杨酸苄基酯;苯基乙基水杨酸酯;甲基-2,4-二羟基-3,6-二甲基苯甲酸酯;乙基-3-苯基甘油酸酯;乙基-3-甲基-3-苯基甘油酸酯;
-含氮的芳香族化合物,例如2,4,6-三硝基-1,3-二甲基-5-叔丁基苯;3,5-二硝基-2,6-二甲基-4-叔丁基苯乙酮;肉桂酸腈;5-苯基-3-甲基-2-戊烯酸腈;5-苯基-3-甲基戊烯酸腈;氨基苯甲酸甲酯;甲基-N-甲基氨基苯甲酸酯;氨基苯甲酸甲酯与7-羟基-3,7-二甲基辛醛、2-甲基-3-(4-叔丁基苯基)丙醛或2,4-二甲基-3-环己烯甲醛的席夫碱;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;吲哚;粪臭素;2-甲氧基-3-异丙基吡嗪;2-异丁基-3-甲氧基吡嗪;4-(4,8-二甲基-3,7-壬二烯基)-吡啶;
-酚、苯基醚和苯基酯,例如草蒿脑;茴香脑;丁香油酚;丁香酚基甲基醚;异丁子香酚;异丁子香基甲基醚;百里香酚;香芹酚;二苯基醚;β-萘基甲基醚;β-萘基乙基醚;β-萘基异丁基醚;1,4-二甲氧基苯;丁香酚基乙酸酯;2-甲氧基-4-甲基苯酚;2-乙氧基-5-(1-丙烯基)苯酚;对甲苯基苯基乙酸酯;来自杂环化合物的组,例如2,5-二甲基-4-羟基-2H-呋喃-3-酮;2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮;3-羟基-2-甲基-4H-吡喃-4-酮;2-乙基-3-羟基-4H-吡喃-4-酮;
-内酯,例如1,4-辛内酯;3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸烯-1,4-内酯;1,4-十一碳内酯;1,4-十二碳内酯;1,5-癸内酯;1,5-十二碳内酯;1,15-十五碳内酯;顺式和反式-11-十五碳烯-1,15-内酯;顺式和反式-12-十五碳烯-1,15-内酯;1,16-十六碳内酯;9-十六碳烯-1,16-内酯;10-氧杂-1,16-十六碳内酯;11-氧杂-1,16-十六碳内酯;12-氧杂-1,16-十六碳内酯;1,12-十二碳二酸乙烯酯;1,13-十三碳二酸乙烯酯;香豆素;2,3-二氢香豆素;八氢香豆素;
以及上述物质的立体异构体、对映异构体、位置异构体、非对映异构体、顺/反异构体或差向异构体。
在一个替代实施方式中,将香味油或香水油用作芯材料。这涉及包含至少一种香味剂的组合物。此类组合物,尤其香味油或香水油,优选包括两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种香味剂。香味油或香水油优选选自来自天然原料的提取物的组,如精油、冷凝酯、净油、树脂、类树脂、香胶、酊剂,例如龙涎香酊;香树油;当归种子油;当归根油;大茴香油;缬草油;罗勒油;树苔净油;月桂叶油;艾蒿油;安息香树脂;佛手柑油;蜂蜡净油;桦焦油;苦杏仁油;香薄荷油;布枯叶油;香脂豆木油;杜松油;菖蒲油;樟脑油;依兰依兰油;豆蔻油;苦香树皮油;黑醋栗油;黑醋栗净油;海狸香净油;柏叶油;柏木油;岩蔷薇油;香茅油;柠檬油;苦配巴香膏;苦配巴香膏油;香菜油;闭鞘姜根油;孜然油;奠柏油;茚蒿油;莳萝草油;莳萝籽油;苦橙花叶水净油;橡树苔净油;榄香脂油;龙蒿油;柠檬桉油;桉树油;小茴香油;云杉针油;白松香油;白松香树脂;天竺葵油;葡萄柚油;愈创木油;古云香膏;古云香膏油,永久花净油;永久花油;姜油;鸢尾根净油;鸢尾根油;茉莉净油;菖蒲油;洋甘菊油,蓝色;洋甘菊油,罗马;胡萝卜种子油;苦香树皮油;松针油;留兰香油;葛缕子油;赖百当油;赖百当净油;赖百当树脂;醒目薰衣草净油;醒目薰衣草油;薰衣草净油;薰衣草油;柠檬草油;独活草油;蒸馏酸橙油;压榨酸橙油;芳樟醇;山苍子油;月桂叶油;肉豆蔻油;墨角兰油;橘子油;马尾松油;含羞草净油;麝香颗粒油;麝香酊剂;香紫苏油;肉豆蔻油;没药净油;没药油;桃金娘油;康乃馨叶油;康乃馨花油;橙花油;乳香净油;乳香油;金合欢油;橙花净油;橙子油;牛至油;玫瑰草油;广藿香油;紫苏油;秘鲁香膏油;欧芹叶油;欧芹籽油;苦橙叶油;薄荷油;胡椒油;西班牙椒油;松油;波莱油;玫瑰净油;玫瑰木油;玫瑰油;迷迭香油;鼠尾草油,达尔马提亚;鼠尾草油,西班牙;檀木油;芹菜籽油;穗华薰衣草油;八角茴香油;安息香油;万寿菊油;冷杉针油;茶树油;松脂油;百里香油;妥卢香膏;零陵香净油;晚香玉净油;香草提取物;紫罗兰叶净油;马鞭草油;香根草油;杜松浆果油;葡萄酒酵母油;苦艾油;冬青油;依兰油;牛膝花油;麝猫净油;肉桂叶油;肉桂皮油;及其馏分,或由其中分离出的成分。
在本发明意义上可以被封装的上述单独香味物质或单独香味剂尤其优选用于具有醛、羧酸或酯官能度的香味物质或香味剂。
还包括对应的缩醛以及酯和内酯的醛类香味物质或香味剂可以被细分为如下这些组,即:
(i)脂肪族醛及其缩醛;
(ii)环脂肪族醛;
(iii)芳香族或芳香脂肪族醛;
(iv)脂肪族、芳香族或芳香脂肪族酯;以及
(v)内酯;
以及相应地其混合物。
上述具有醛、羧酸或酯官能度的香味物质或香味剂以及其混合物选自下组中的一项或多项:
-脂肪醛及其缩醛,例如己醛;庚醛;辛醛;壬醛;癸醛;十一碳醛;十二碳醛;十三碳醛;2-甲基辛醛;2-甲基壬醛;(f)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一碳烯醛;(f)-4-癸烯醛;2-十二碳烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛-二乙基缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅基氧基乙醛;
-环脂肪族醛,例如2,4-二甲基-3-环己烯甲醛;2-甲基-4-(2,2,6-三甲基-环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
-芳香族和芳香脂肪族醛,例如苯甲醛;苯基乙醛;3-苯基丙醛;氢化阿托醛;4-甲基苯甲醛;4-甲基苯基乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)-丙醛;2-甲基-3-(4-叔丁基苯基)丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛;α-戊基肉桂醛;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧苯甲醛;3,4-二甲氧基苯甲醛;2-甲基3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧苯基)丙醛;
-脂肪族羧酸酯,例如(E)-和(Z)-3-己烯醇甲酸酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;3,5,5-三甲基己基乙酸酯;3-甲基-2-丁烯基乙酸酯;(f)-2-己烯基乙酸酯;(E)-和(Z)-3-己烯基乙酸酯;乙酸辛酯;3-辛基乙酸酯;1-辛烯-3-基乙酸酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)-和(Z)-3-己烯醇异丁酸酯;巴豆酸己酯;异戊酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;乙基-(E,Z)-2,4-癸二烯酸酯;2-辛炔酸甲酯;2-壬炔酸甲酯;2-异戊氧基乙酸烯丙酯;甲基-3,7-二甲基-2,6-辛二烯酸酯;
-环状醇的酯,例如2-叔丁基环己基乙酸酯;4-叔丁基环己基乙酸酯;2-叔戊基环己基乙酸酯;4-叔戊基环己基乙酸酯;十氢-2-萘基乙酸酯;3-戊基四氢-2H-吡喃-4-基乙酸酯;十氢-2,5,5,8a-四甲基-2-萘基乙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5-或-6-茚基乙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5-或-6-茚基丙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5-或-6-茚基异丁酸酯;4,7-甲桥八氢-5-或-6-茚基乙酸酯;
-芳香脂肪族醇与脂肪族羧酸的酯,例如苄基乙酸酯;丙酸苄基酯;异丁酸苄基酯;异戊酸苄基酯;2-苯基乙基乙酸酯;2-苯基乙基丙酸酯;2-苯基乙基异丁酸酯;2-苯基乙基异戊酸酯;1-苯基乙基乙酸酯;α-三氯甲基苄基乙酸酯;α,α-二甲基苯基乙基乙酸酯;α,α-二甲基苯基乙基丁酸酯;乙酸肉桂基酯;2-苯氧基乙基异丁酸酯;4-甲氧基苄基乙酸酯;
-环脂肪族羧酸的酯,例如烯丙基-3-环己基丙酸酯;烯丙基环己氧基乙酸酯;二氢茉莉酮酸甲酯;茉莉酮酸甲酯;甲基-2-己基-3-氧代环戊烷羧酸酯;乙基-2-乙基-6,6-二甲基-2-环己烯羧酸酯;乙基-2,3,6,6-四甲基-2-环己烯羧酸酯;乙基-2-甲基-1,3-二氧戊环-2-乙酸酯;
-芳香族和芳香脂肪族羧酸酯,例如苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄基酯;甲基苯基乙酸酯;乙基苯基乙酸酯;香叶基苯基乙酸酯;苯基乙基苯基乙酸酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄基酯;苯基乙基肉桂酸酯;肉桂酸肉桂基酯;烯丙基苯氧基乙酸酯;水杨酸甲酯;异戊基水杨酸酯;水杨酸己酯;水杨酸环己酯;顺式-3-己烯基水杨酸酯;水杨酸苄基酯;苯基乙基水杨酸酯;甲基-2,4-二羟基-3,6-二甲基苯甲酸酯;乙基-3-苯基甘油酸酯;乙基-3-甲基-3-苯基甘油酸酯。
下面以其商品名称列出了在本发明方法中特别优选作为基团(i)至(v)代表物的醛、缩醛、酯和内酯:
醛:2-甲基戊醛;醛C12 MNA HM;醛C 4;醛C 5;醛C 6;醛C 7;醛C 8;醛C 9;醛C10;醛C11ISO;醛C11MOA PURE;醛C11十一碳醛;醛C11十一烯;醛C12;醛C12MNA;醛C13;红桔醛(ALDEHYDE MADARINE);戊基肉桂醛α;茴香醛-O;茴香醛;天然苯甲醛;香柠檬醛;巴豆醛;BOURGENOAL;崁酮醛;柠檬醛;香茅醛HM;香茅基氧代乙酰醛;白柠檬醛;白柠檬醛E HM;皮质醛;皮质醛50PCT PEMOSA;巴豆醛;枯茗醛;仙客来醛;癸二烯醛,反式、反式-2,4,癸醛,顺式-4;癸醛,反式-2;天然癸醛,反式-2;癸醛,反式-4;癸醛-9,1;十二碳二烯醛2,6;十二碳醛,反式-2;道比卡尔(DUPICAL);环氧癸醛-4,5-2 10%TRI;乙基己醛;花青醛;香叶醛;新洋茉莉醛;HELIOPAN;洋茉莉醛;庚二烯,反式,反式2-4;庚醛,顺式-4;庚醛,反式-2;己醛,反式-2;己基肉桂醛α;龙葵醛;羟基香茅醛;特制异十一醛;异壬醛;异戊醛;柠檬醛H&R JS I;铃兰醛;亚油醛(LINOLAL);新铃兰醛;MAJANTAL;红橘醛;TEC BHT中10%的红橘醛;梅弗兰醛;甲基香茅醛(METHODY CITRONELLAL);甲基丁醛;甲基肉桂醛α;甲基苯基戊醛-4,2,2;甲基硫代丙醛-3;甲基三癸醛-12 10%VT;甲基-3-丁烯-2-醛;甲基-5-苯基-2-己烯-2-醛;MUGENAL 50DPG;新环柠檬醛;壬二烯醛;反式,顺式-2,6;壬烯醛,顺式-6;壬烯醛,反式-2;3/060251;戊醛,反式-2;紫苏醛;苯基乙醛;苯基丁醛,反式-2,2;苯基丙醛;松乙醛;PROFRANESAL;丙醛2-(对甲苯基);丙醛;新PS紫萝酮(IRALDEIN)X;藏红花醛;水杨醛FG;SILVIAL;四氢柠檬醛;惕各醛-2,2;对位甲苯醛FG;三癸醛,反式-2;新女贞醛;十一碳二烯醛-2,4;十一碳醛,反式-2;鲜草醛;女贞醛;VERTOMUGAL;VERTIPRENAL;VETRAL ROH;天然肉桂醛HM;缩醛:弗罗派;庚醛二乙基缩醛;壬二烯醛二乙基缩醛;奥古烷;苯乙醛甘油缩醛;本乙醛二甲基缩醛;酯:乙酸茉莉酯;茉莉呋喃;二氢茉莉酮酸甲酯(KHARISMAL);
在本发明方法的另一个变体中还可以以单独芳香剂的形式封装作为芯材料的芳香物质,其中芯材料包括至少一种单独芳香物质或其混合物。
在本发明的意义上可以被封装的芳香物质的典型例子选自由以下项组成的组:苯乙酮;烯丙基己酸酯;α-紫罗兰酮;β-紫罗兰酮;茴香醛;乙酸茴香酯;甲酸茴香酯;苯甲醛;苯并噻唑;苄基乙酸酯;苄基醇;苯甲酸苄基酯;β-紫罗兰酮;丁酸丁酯;己酸丁酯;丁烯基苯酞;香芹酮;莰烯;石竹烯;桉叶素;乙酸肉桂基酯;柠檬醛;香茅醇;香茅醛;乙酸香茅酯;乙酸环己酯;伞花烃;大马酮;癸内酯;二氢香豆素;邻氨基苯甲酸二甲酯;邻氨基苯甲酸二甲酯;十二碳内酯;乙酸乙氧基乙酯丁酸乙酯;丁酸乙酯;癸酸乙酯;己酸乙酯;巴豆酸乙酯;乙基呋喃酮;乙基愈创木酚;异丁酸乙酯;异戊酸乙酯;乳酸乙酯;甲基丁酸乙酯;丙酸乙酯;桉叶油醇;丁香油酚;庚酸乙酯;4-(对羟基苯基)-2-丁酮;γ-癸内酯;香叶醇;乙酸香叶酯;乙酸香叶酯;葡萄柚醛;二氢茉莉酸甲酯(例如);洋茉莉醛;2-庚酮;3-庚酮;4-庚酮;反式-2-庚烯醛;顺式-4-庚烯醛;反式-2-己烯醛;顺式-3-己烯醇;反式-2-己烯酸;反式-3-己烯酸;顺式-2-己烯基乙酸酯;顺式-3-己烯基乙酸酯;顺式-3-己烯基己酸酯;反式-2-己烯基己酸酯;顺式-3-己烯基甲酸酯;顺式-2-己烯基乙酸酯;顺式-3-己基乙酸酯;反式-2-己基己酸酯;顺式-3-己基甲酸酯;对羟基苄基丙酮;异戊醇;异戊酸异戊酯;丁酸异丁酯;异丁醛;异丁香油酚甲基醚;异丙基甲基噻唑;月桂酸;乙酰丙酸;芳樟醇;芳樟醇氧化物;乙酸芳樟酯;薄荷醇;薄荷呋喃;氨基苯甲酸甲酯;甲基丁醇;甲基丁酸;2-甲基丁基乙酸酯;己酸甲酯;肉桂酸甲酯;5-甲基糠醛;3,2,2-甲基环戊烯醇酮;6,5,2-甲基庚烯酮;二氢茉莉酮酸甲酯;茉莉酮酸甲酯;2-甲基甲基丁酸酯;2-甲基-2-戊烯醇酸;硫代丁酸甲酯;3,1-甲基硫代己醇;3-甲基硫代己基乙酸酯;橙花醇;乙酸橙花酯;反式,反式-2,4-壬二烯醛;2,4-壬二烯醇;2,6-壬二烯醇;2,4-壬二烯醇;诺卡酮;δ-辛内酯;γ-辛内酯;2-辛醇;3-辛醇;1,3-辛醇;1-辛基乙酸酯;3-辛基乙酸酯;棕榈酸;副醛;水芹烯;戊二酮;苯基乙基乙酸酯;苯基乙基醇;苯基乙基醇;苯基乙基异戊酸酯;胡椒醛;丙醛;丁酸丙酯;胡薄荷酮;胡薄荷醇;甜橙醛;硫噻唑;萜烯;萜品醇;萜品油烯;8,3-硫代薄荷酮;4,4,2-硫代甲基戊酮;百里香酚;δ-十一碳内酯;γ-十一碳内酯;巴伦西亚桔烯;戊酸;香草醛;乙偶姻;乙基香草醛;异丁酸乙基香草醛酯(3-乙氧基-4-异丁酰基氧代苯甲醛);2,5-二甲基-4-羟基-3(2H)-呋喃酮及其衍生物(优选酱油酮(2-乙基-4-羟基-5-甲基-3(2H)-呋喃酮)、高呋喃酮2-乙基-5-甲基-4-羟基-3(2H)-呋喃酮和5-乙基-2-甲基-4-羟基-3(2H)-呋喃酮);麦芽酚和麦芽酚衍生物(优选乙基麦芽酚);香豆素和香豆素衍生物;γ-内酯(优选γ-十一碳内酯、γ-壬内酯、γ-癸内酯);δ-内酯(优选4-甲基δ癸内酯、二氢戊基吡喃、δ-癸内酯、晚香玉种内酯(Tuberolacton));山梨酸甲酯;二香草醛(Divanillin);4-羟基-2(或5)-乙基-5(或2)-甲基-3(2H)呋喃酮;2-羟基-3-甲基-2-环戊烯酮;3-羟基-4,5-二甲基-2(5H)-呋喃酮;乙酸异戊酯;丁酸乙酯;乙酸正丁酯;丁酸异戊酯;3-甲基-丁酸乙酯;正己酸乙酯;正己酸烯丙酯;正己酸正丁酯;正辛酸乙酯;乙基-3-甲基-3-苯基甘油酸酯;乙基-2-反式-4-顺式-癸二烯酸酯;4-(对羟基苯基)-2-丁酮;1,1-二甲氧基-2,2,5-三甲基-4-己烷;2,6-二甲基-5-庚烯-1-醛;苯基乙醛;2-甲基-3-(甲基硫代)呋喃;2-甲基-3-呋喃硫醇;双(2-甲基-3-糠基)二硫化物;糠基硫醇;甲硫基丙醛;2-乙酰基-2-噻唑啉;3-巯基-2-戊酮;2,5-二甲基-3-呋喃硫醇;2,4,5-三甲基噻唑;2-乙酰基噻唑;2,4-二甲基-5-乙基噻唑;2-乙酰基-1-吡咯啉;2-甲基-3-乙基吡嗪;2-乙基-3,5-二甲基吡嗪;2-乙基-3,6-二甲基吡嗪;2,3-二乙基-5-甲基吡嗪;3-异丙基-2-甲氧基吡嗪;3-异丁基-2-甲氧基吡嗪;2-乙酰基吡嗪;2-戊基吡啶;(E,E)-2,4-癸二烯醛;(E,E)-2,4-壬二烯醛;(E)-2-辛烯醛;(E)-2-壬烯醛;2-十一碳烯醛;12-甲基十三碳醛;1-戊烯-3-酮;4-羟基-2,5-二甲基-3(2H)-呋喃酮;愈创木酚;3-羟基-4,5-二甲基-2(5H)-呋喃酮;3-羟基-4-甲基-5-乙基-2(5H)-呋喃酮;肉桂醛;肉桂醇;水杨酸甲酯;异胡薄荷醇以及这些物质的在本文中未明确提及的立体异构体、对映异构体、位置异构体、非对映异构体、顺/反异构体或差向异构体。
最优选地,在制备基于异氰酸酯的微胶囊时应用选自由以下项组成的组的香味物质或香味剂或芳香物质:AGRUMEX LC;香茅腈;醛C11十一碳醛;醛C12月桂醛;醛C12 MNA;醛C14 SOG;醛C16 SOG;烯丙基异戊氧基乙酸酯;烯丙基己酸酯;烯丙基环己基丙酸酯;烯丙基庚酸酯;木质龙涎香10TEC;木质龙涎香晶体10%IPM;降龙涎醚;来自大茴香的天然茴香脑;纯的茴香醛;;苄内酯;水杨酸苄酯;冰片L/异冰片65/35;布枯叶油;香茅醇950;爽腈(CLONAL);水杨酸环己酯;上(SUPRA)对位伞花烃;大马酮δ;二氢月桂烯醇;丁酸二甲基苄基原酯;王朝酮;十三烷二酸环乙撑酯;乙基甲基丁酸酯-2;乙基藏红花酸酯;天然桉叶油醇;蓝桉叶油80/85%;天然丁香油酚;甜型天然芳香茴香油;榛子酮10%IPM;榛子酮;弗罗派;格蓬酮;香叶醇60;二氢茉莉酮酸甲酯;乙酸三环癸烯酯;香菠酯;丙酸三环癸烯酯;己烯基乙酸酯,顺式-3;己烯基水杨酸酯,顺式-3;乙酸己酯;乙酸己酯S;异丁酸己酯;水杨酸己酯;丁酸异戊酯;乙酸异冰片酯;异丙基甲基丁酸酯-2;异甲基紫罗兰酮70;爪哇檀香;樟脑(KAMPFER)DL;甲酚甲基醚P(CR<10PPM);柠檬腈;女贞醛;铃兰醛;芳樟醇;母菊酯;甜瓜醛;甲基庚炔碳酸酯;甲基辛炔碳酸酯;麝香烯酮;新环柠檬醛;橙花素;萘甲醚晶体;橙花酮;赛木香醇;橙油;环己酮;十三烯腈(OZONIL);广藿香油ENTF.;植物油甘油三酯;来自桉树油的水芹烯级分;苯基乙基乙酸酯;高顺式玫瑰醚;苯乙烯基乙酸酯;萜烯γ;四氢芳樟醇;TIMBERSILK;柠檬酸三乙酯;甲基癸烯醇;女贞醛;甲基柏木烯酮;K和上述有效成分的混合物。
在本发明方法的另一个变体中还可以封装作为芯材料的生物源成分,其中芯材料包括至少一种生物源成分或其混合物。
生物源成分应理解为具有生物活性的有效成分,例如生育酚、生育酚乙酸酯、生育酚棕榈酸酯、抗坏血酸、樱草黄、肌肽、咖啡因、(脱氧)核糖核酸及其碎裂产物、β-葡聚糖、视黄醇、红没药醇、尿囊素、植烷三醇、泛醇、AHA酸、氨基酸、神经酰胺、伪神经酰胺、精华油、植物提取物、以及复合维生素。
在本发明的用于制备基于异氰酸酯的微胶囊的方法中,首先将上述包含至少两个异氰酸酯或异硫氰酸酯基团的单体与待封装的疏水有效成分一起溶解在惰性的溶剂或溶剂混合物中。如此构成的有机的疏水的油相构成内部的非水相。
作为由于内部的非水相的惰性溶剂可以提及:氯化的联苯、氯化的石蜡、植物油例如棉籽油、花生油、棕榈油、三甲苯基磷酸酯、硅酮油、二烷基邻苯二甲酸酯、二烷基己二酸酯、部分氢化的三联苯、烷基化的联苯、烷基化的萘、二芳基醚、芳基烷基醚和高级烷基化的苯、苯甲酸苄基酯、豆蔻酸异丙酯以及这些疏水溶剂的任意混合物以及这些疏水溶剂中的单种或多种与煤油、石蜡和/或异石蜡的混合物。优选地使用植物油-甘油三酯、苯甲酸苄基酯或豆蔻酸异丙酯作为用于提供内部的非水相的溶剂。
相对于内部的非水相的总重量,内部的非水相例如可以包含20至50重量%、优选25至45重量%且仍更优选33至40重量%的待封装的疏水的有效成分,1至8重量%、优选3至7重量%且仍更优选5至6重量%的异氰酸酯,以及补充到100重量%的疏水的溶剂。
包括至少一种具有两个或更多个异氰酸酯基团以及至少一种疏水的有效成分的内部非水相在外部的水相或亲水相中乳化,同时形成水包油乳液。
外部的水相包括至少一种保护胶体和至少一种催化剂。
保护胶体为如下的化合物:所述化合物在沉淀反应中,也就是说在从均匀的液相中沉淀出固相时,防止主要颗粒的结块(聚结、聚集、成絮、絮凝)。保护胶体以其疏水部分支撑在主要颗粒处并且将其极性(也就是说亲水的分子部分)朝向水相。通过支撑在表面处,降低了界面张力并且防止主要颗粒的聚结。另外,这稳定了乳液并且同时有利于构成相对较小的小液滴并因此还有利于构成对应的微胶囊。
在根据本发明的第一方面的本发明方法中使用的保护胶体选自由以下项组成的组:二醇,尤其乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、丁二醇异构体、1,2-戊二醇、1,2-己二醇、1,2-辛二醇、1,2-癸二醇、1,2-十二烷二醇,和多元醇,尤其三醇,例如甘油及其乙氧基化产物和丙氧基化产物,三羟甲基丙烷及其乙氧基化产物和丙氧基化产物,聚乙烯醇及其衍生物,例如铵官能化或磺酸根官能化的聚乙烯醇,多酚,尤其1,3,5-三羟基苯,淀粉,尤其来自小麦、土豆、玉米、大米、木薯或燕麦的淀粉,或者化学、机械和/或酶改性的淀粉,以及上述化合物的混合物。
最优选使用多元醇、多酚或淀粉、尤其改性淀粉作为保护胶体。特别优选地将聚乙烯醇或其铵衍生物、1,3,5-三羟基苯或改性淀粉作为保护胶体用于制备本发明的微胶囊。
先前提及的化合物具有双重功能:一方面它们与异氰酸酯反应,由此形成稳定的微胶囊,并且另一方面它们用作保护胶体,其方式为防止固态颗粒的聚结、稳定乳液并由此促进小液滴的形成。
出人意料且已经证实为特别有利的是,在外部的水相中将上述保护胶体之一与淀粉或改性淀粉组合用作另外的保护胶体。通过此类的组合促进了在保护胶体与异氰酸酯之间的反应。
最优选的是组合使用保护胶体和改性淀粉。使用上述组合一方面具有以下优点,即,固相在配方中不会成絮并且乳液得以稳定,而另一方面这种共用产生了特别稳定的微胶囊。
多酚(优选1,3,5-三羟基苯)与淀粉或改性淀粉已经被证实为特别有利的组合。最优选的是1,3,5-三羟基苯与改性淀粉的组合。
1,3,5-三羟基苯用作羟基供体,以便在没有羟基的保护胶体中提供对应的基团并由此保证获得稳定性。
相对于外部的水相的总重量,所使用的保护胶体的量或者所使用的保护胶体组合的量在1至8重量%的范围内、优选在2至4重量%的范围内、仍更优选在3至4重量%的范围内。
在外部的水相中的保护胶体与在内部的非水相中的异氰酸酯或异硫氰酸酯之比在1:5至1:100的范围内、优选在1:10至1:75的范围内、仍更优选在1:25至1:50的范围内。
在本发明方法中用在外部的水相中的催化剂优选为二氮杂二环[2.2.2]辛烷(DABCO)。DABCO,也被称为三亚乙基二胺(TEDA),是双环的叔胺。DABCO用作用于制备聚氨酯塑料的催化剂。具有自由电子对的叔胺有助于内部的非水相中的异氰酸酯与在外部的水相中的保护胶体之间的反应。
相对于外部的水相的总重量,加入到外部的水相中的催化剂的量在0.001至1重量%的范围内、优选在0.02至0.75重量%的范围内并且特别优选在0.05至0.5重量%的范围内。但是在聚合进行较慢时也可以增加催化剂。
(在液态有效成分情况下的)乳液形成或(在固态有效成分情况下的)悬浮液形成,也就是说内部的非水相或油相与外部的水相或亲水相的乳化或悬浮,在大湍流或强剪切下进行,其中湍流或剪切的强度决定所获得的微胶囊的直径。微胶囊的制备在此可以连续地或不连续地进行。胶囊的尺寸一般随着水相的黏度增大或随着油相的黏度减小而减小。
出人意料地已经确定,在保护胶体(优选多元醇)的存在下,在内部的非水相乳化或悬浮在外部的水相中时,在被乳化或被悬浮的待封装的疏水颗粒(构成本发明微胶囊的芯)的界面处,通过界面聚合在芯附近形成了胶囊壳或胶囊壁。这种形成是基于多异氰酸酯与保护胶体(优选多元醇)的多加成反应,同时由根据下式的聚氨酯构成胶囊壳或胶囊壁:
O=C=N-R-N=C=O+-(CH2-CH(OH)-)n-→-(R-O-CO-NH-R-NH-CO-O-)n
这通过形成和释放一氧化碳而显示出来。
可能有利的是,为了制备根据本发明的基于异氰酸酯的微胶囊,外部的水相任选地以溶解或分散的方式包含其他的保护胶体和/或稳定剂和/或乳化助剂。这样的试剂可以相对于水相的总重量例如以0.05至5重量%、优选0.1至4重量%的量添加。
外部的水相另外优选包含稳定剂,所述稳定剂使乳液/浆料稳定,以防止内部的非水(油)相与外部的水相分离(Entmischung)。用于制备根据本发明的基于异氰酸酯的微胶囊的优选稳定剂主要是具有磺酸根基团的丙烯酸共聚物。同样适合的是丙烯酰胺和丙烯酸的共聚物、烷基丙烯酸酯和N-乙烯基吡咯烷酮的共聚物,例如K15,K30或K90(BASF);多羧酸钠、聚苯乙烯磺酸钠、乙烯基和甲基乙烯基醚-马来酸酐共聚物以及乙烯-、异丁烯-或苯乙烯-马来酸酐共聚物、微晶纤维素(例如在名称下有售)、定优胶(Diutan Gum)、黄原胶或羧甲基纤维素。
稳定剂的用量可以分别相对于外部的水相在0.01至10重量%范围内且尤其在0.1至3重量%范围内。
任选地,在本发明的方法中,使用乳化剂、优选O/W乳化剂,所述乳化剂使内部的非水相的小油滴能够均匀分布在外部的水相中并且稳定乳液。类似的内容适用于固态的不可溶的有效成分在外部的水相中的稀释,以便稳定由此获得的悬浮液。
例如可以考虑将来自下组中的至少一项的非离子型表面活性剂作为乳化剂:
-2至30Mol环氧乙烷和/或0至5Mol环氧丙烷到具有8至22个C原子的直链脂肪醇上、到具有12至22个C原子的脂肪酸上、到在烷基中具有8至15个C原子的烷基酚上以及到在烷基残基中具有8至22个碳原子的烷基胺上的加成产物;
-在烷(烯)基残基中具有8至22个的烷基低聚糖苷和/或烯基低聚糖苷及其乙氧基化的类似物;
-1至15Mol环氧乙烷到蓖麻油和/或固化蓖麻油上的加成产物;
-15至60Mol环氧乙烷到蓖麻油和/或固化蓖麻油上的加成产物;
-甘油和/或山梨聚糖与具有12至22个碳原子的不饱和的直链的或饱和的支链的脂肪酸和/或具有3至18个碳原子的羟基羧酸的偏酯,及其与1至30Mol环氧乙烷的加成产物;
-聚甘油(平均自缩合度2至8)、聚乙二醇(分子量400至5000)、三羟甲基丙烷、季戊四醇、糖醇(例如山梨糖醇)、烷基葡萄糖苷(例如甲基葡萄糖苷、丁基葡萄糖苷、月桂基葡萄糖苷)以及聚葡萄糖苷(例如纤维素)与具有12至22个碳原子的饱和和/或不饱和的、直链或支链的脂肪酸和/或具有3至18个碳原子的羟基羧酸的偏酯,及其与1至30Mol环氧乙烷(优选)的加成产物;
-季戊四醇、脂肪酸、柠檬酸和脂肪醇的混合酯和/或具有6至22个碳原子的脂肪酸、甲基葡萄糖苷和多元醇(优选甘油或聚甘油)的混合酯;
-单、二、和三烷基磷酸酯以及单、二和/或三PEG烷基磷酸酯及其盐;
-羊毛蜡醇;
-聚硅氧烷-聚烷基-聚醚共聚物或者对应的衍生物;嵌段共聚物,例如聚乙二醇-30二聚羟基硬脂酸酯;聚合物乳化剂,例如来自Goodrich的Pemulen型(TR-1,TR-2)或者来自Cognis的SP;
-聚亚烷基二醇以及碳酸甘油酯。
可以在用于制备基于异氰酸酯的微胶囊的本发明方法中使用的典型的阴离子型乳化剂为具有12至22个碳原子的脂肪族脂肪酸,例如棕榈酸、硬脂酸或山嵛酸,以及具有12至22个碳原子的二羧酸,例如壬二酸或癸二酸。
另外,在用于制备基于异氰酸酯的微胶囊的本发明方法中可以使用两性离子型表面活性剂作为乳化剂。两性离子型表面活性剂是指如下的表面活性化合物:所述化合物在分子中携带有至少一个季铵基团和至少一个羧酸根或磺酸根基团。特别适合的两性离子表面活性剂是所谓的甜菜碱,如N-烷基-N,N-二甲基甘氨酸铵,例如椰油烷基二甲基甘氨酸铵,N-酰氨基丙基-N,N-二甲基甘氨酸铵,例如椰油酰氨基丙基二甲基甘氨酸铵,以及分别在烷基或酰基中具有8至18个C原子的2-烷基-3-羧甲基-3-羟基乙基咪唑啉和椰油酰氨基乙基羟基乙基羧甲基甘氨酸盐。特别优选的是在CTFA名称椰油酰氨基丙基甜菜碱下已知的脂肪酸酰胺衍生物。同样适合的乳化剂是两性电解质型的表面活性剂。两性电解质型的表面活性剂理解为如下的表面活性化合物:所述化合物除了C8/18烷基或酰基之外在分子中还包含至少一个游离氨基和至少一个-COOH-或-SO3H-基团,并且能够用于形成内盐。适合的两性电解质型表面活性剂的例子为在烷基中分别具有约8至18个C原子的N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚酰胺基二丙酸、N-羟乙基-N-烷基酰胺基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸。特别优选的两性电解质型表面活性剂为N-椰油烷基氨基丙酸、椰油酰氨基乙基氨基丙酸盐和C12/18酰基肌氨酸。最后还可以考虑阳离子表面活性剂作为乳化剂,其中酯基季铵盐类型的特别优选的,优选甲基季铵化的二脂肪酸三乙醇胺酯盐。
分别相对于外部的水相的总重量,乳化剂可以以约0.5至约10重量%的量且优选约1至约5重量%的量加入外部的水相中。
本发明的用于制备微胶囊分散体的方法例如可以根据“在线”技术来进行。在此,借助于强制计量泵首先在1200至1500l/h的流过体积下将内部的非水相和外部的水相分开地送入乳化涡轮机中,在引入到乳化涡轮机之前不久合并或者在乳化涡轮机中合并。
内部的非水相与外部的水相的重量比优选在10:90至60:40的范围内、优选在30:70至50:50的范围内。
此外,用于制备基于异氰酸酯的微胶囊的本发明方法还可以在常见的分散设备或乳化设备中进行。
在本发明方法中的乳化或分散过程有利地进行0.5至10分钟、优选0.75至4分钟且非常特别优选1至2.5分钟,直至已经设定10至50μm±5μm的胶囊尺寸。
在本发明方法的一个后续步骤中,在1000至1500rpm搅拌速度、优选在1200rpm搅拌速度的搅拌下进行胶囊壳或胶囊壁材料的第一交联。第一交联通过加入在酸性pH值下反应的胺来进行,以便使包围芯材料的胶囊壳交联并且变得稳定。
当第一交联用胺在2至7的酸性pH值下进行、优选在2至6的pH值下进行并且最优选在3至5的略微酸性的pH值下进行时,实现了关于胶囊壳形成的特别有利的结果。为此向外部的水相加入酸,例如甲酸或乙酸,并且将pH值设定到上述范围内。
相对于在碱性环境中的交联,在酸性pH值范围内进行第一交联的优点是,具有醛、羧酸或酯官能团的疏水的有效成分在异氰酸酯或异硫氰酸酯交联的前几个反应步骤中不会皂化。
由此防止这种或这些待封装的有效成分(例如香水油)在化学上发生改变并随之一方面引起有效成分损失且另一方面使乳液变得不稳定。
第一交联的步骤仍更优选在20℃至30℃的温度下进行。
在酸性pH值下反应的胺选自由碱性氨基酸及其盐酸盐、尤其赖氨酸盐酸盐和鸟氨酸盐酸盐组成的组。最优选的是赖氨酸盐酸盐作为交联剂。
第一交联剂原样地(例如作为固体)或者以水溶液形式加入乳液中。
第一交联剂以0.5至2Mol/l、优选1Mol/l的浓度被包含在水溶液中。溶液具有4至7的pH值。
在本发明方法中的第一交联进行约10分钟至20分钟的时间段、优选12至18分钟的时间段且最优选约15分钟的时间段。
在第一交联步骤之后是通过加入在碱性pH值下反应的胺使胶囊壳或胶囊壁的材料进一步交联的步骤,同时形成聚脲基质。
当进一步交联用在碱性pH值下反应的胺在7至14的碱性pH值下进行、优选在7至10的碱性pH值下进行并且最优选在7至8的略微碱性的pH值下进行时,实现了关于胶囊形成的特别有利的结果。
进一步交联的步骤仍更优选在35℃至50℃的温度下进行。
所述在碱性pH值下反应的胺选自由二胺、三胺和多元胺以及碳酸胍组成的组。最优选的是碳酸胍作为进一步交联剂。
进一步交联剂原样地(例如作为固体)或者以水溶液形式加入乳液中。
进一步交联剂以0.5至2Mol/l、优选1Mol/l的浓度被包含在水溶液中。溶液具有7至14的pH值、优选12的pH值。
通过加入在碱性pH值下反应的胺,将乳液的pH值向较高pH值推移。最终产物(也就是说最终的胶囊浆料)的pH值为5至8、优选为6至7的pH值。
因此,根据本发明制备基于异氰酸酯微胶囊的重要特征是,第一交联在酸性pH值下进行,并且随后的进一步交联在碱性pH值下进行。
通过pH值梯度,在第一交联中、优选在酸性pH值下首先构成具有直链聚脲基质的胶囊壳。在随后的进一步交联中、优选在碱性pH值下将胶囊壳进一步交联并且构成空间交联的聚脲基质。
在这两个交联步骤期间将搅拌功率降低,例如降低到约800至1200rpm的搅拌速度,以免使所形成的微胶囊马上再次被粉碎。
在胶囊壳或胶囊壁完全交联和形成之后,根据本发明方法制备的胶囊作为呈水性分散体或浆料形式的粗微胶囊存在。
在交联之后,微胶囊在浆料中仍然具有柔性壳,所述壳不具有特别的稳定性并且因此容易破碎。为此对壳进行硬化。硬化通过改变温度来触发,其方式为将浆料逐步升温到70℃的温度、优选升温到在60至65℃范围内的温度。硬化通常进行2至4小时的时间段。
附加地有利的是,向外部的水相中加入用于硬化的物质。为此目的使用单宁类的天然植物鞣制剂,在化学上看它们为原花青素类,如特别在热带和亚热带地区在双子叶草本植物、灌木和木本植物中存在的。萜烯一般具有在500至3000KDa范围内的分子量。适合的单宁的优选例子为Corigallin。为了进行硬化,将单宁的水性配制品加入到包含粗微胶囊的水性分散体中。通常以相对于微胶囊约0.1至约2重量%且优选约0.5至约1.5重量%的量来加入单宁。
对于微胶囊的可用性而言的一个重要标准是芯材料与胶囊壁材料的重量比。一方面要努力实现尽可能高的芯材料比例,以便能够实现胶囊的尽可能高的使用价值,但是另一方面需要使胶囊具有仍然足够比例的胶囊壁材料,由此确保胶囊的稳定性。
根据本发明已经证实为特别有利的是,所述微胶囊被设计为,使得所述微胶囊具有50:50至90:10、优选70:30至80:20的芯材料与胶囊壁材料的重量比。
在硬化之后,根据本发明方法制备的微胶囊作为水中的分散体存在,还将其称为微胶囊分散体。微胶囊在此形式中基本上已经可以出售;但是,为了防腐的目的,建议将其干燥。
理论上为此可以考虑如冻干的方法,但是优选例如在流化床中喷雾干燥。在此,已经证实为有利的是,在约20至约50℃且优选约40℃的温度下向分散体中加入多糖、优选糊精且尤其麦芽糊精,所述多糖有助于干燥过程并且在此过程中保护胶囊。在此,相对于分散体中的胶囊质量,多糖的用量可以为约50至约150重量%且优选约80至约120重量%。
喷雾干燥自身可以在常规的喷雾设备中连续地或分批地进行,其中入口温度为约170至约200℃并且优选约180至约185℃并且出口温度为约70至约80℃并且优选约72至约78℃。
已经显示出,利用本发明的方法可以封装疏水的有效成分、尤其具有醛、羧酸或酯官能度的疏水的有效成分。所述微胶囊的独特之处在于出色的稳定性和出色的释放能力。
出人意料地已经证明,利用本发明的方法另外还可以用降低最多50%的胶囊壳或胶囊壁材料量来制备微胶囊,而不会由此出现所获得的微胶囊的稳定性的损害或损失,如在下文的实施例中将示出的。由此在相同量的待封装有效成分下可以用减少的异氰酸酯初始物质量来制备微胶囊。
此外,用本发明方法制备的微胶囊不含甲醛。
在另一个方面,本发明涉及根据本发明方法制备的微胶囊。
如从下文的数据中可以看出的,在保护胶体和催化剂的存在下以及基于异氰酸酯的壳材料用在酸性pH值下反应的胺和在碱性pH值下反应的胺的两阶段交联下进行乳化时,产生稳定的微胶囊。尤其产生了具有如下芯材料的稳定的微胶囊,所述芯材料具有高比例的带有醛、羧酸或酯官能度的有效成分。
本发明的微胶囊在图1中放大10倍展示。胶囊壳的构造可以通过光学显微镜来观察。在制备方法开始时可以辨认出小油滴,但是在交联、加热和冷却之后可以辨认出凹入的(eingedellte)微胶囊。
根据本发明方法制备的微胶囊可以通过其尺寸分布的如下参数来表征:
-d(0.1)值:胶囊的10%小于这个值;
-d(0.5)值:胶囊的50%大于这个值,胶囊的50%小于这个值;以及
-d(0.9)值:胶囊的10%大于这个值。
为了确定粒径,在动态过程的范围内,将本发明的微胶囊分散在水中然后借助于激光衍射来确定粒径。取决于胶囊的尺寸,激光束以不同方式被折射并且可以换算成尺寸。为此使用米氏理论。为了进行颗粒测量,使用Malvern Mastersizer 3000。
本发明的微胶囊的特征在于,它们具有10-50μm的d(0.5)值、优选20至30μm的d(0.5)值的粒径分布,如在图2中示出的,并且具有10至120μm的d(0.9)值、优选60至90μm的d(0.9)值的粒径分布。
图3示出根据现有技术制备的微胶囊的粒径分布(d(0.5)值)。对于香水油4和5值得注意的是无法进行尺寸调节。
根据本发明方法制备的微胶囊的独特之处还在于,它们具有对于本发明微胶囊而言特征性地在-5至-15mV的Zeta电位,如在图4和图5中展示的。优选Zeta电位为-10mV。每个微胶囊都具有Zeta电位。Zeta电位不取决于待封装的有效成分、尤其香水油,但是然而取决于胶囊壳的聚合物。基于在制备本发明微胶囊时Zeta电位的变化就可以证明已经构成了新的聚合物或新的壳,因为乳液中颗粒的表面积且由此还有表面电荷(Zeta电位)有所变化。在没有催化剂情况下制备的本发明的微胶囊具有-27mV的Zeta电位。来自现有技术的微胶囊具有±0mV的Zeta电位。在测量的背景下应用了斯莫鲁霍夫斯基(Smoluchowski)理论。为了测量Zeta电位,使用MALVERN Zetasiszer nanoZS。
与通过在分散介质中计量投料的微胶囊产生的信号强度无关,从图4和图5中可以清楚地辨认出,本发明微胶囊的Zeta电位在-5至0mV,因为使用催化剂和与之伴随的聚氨酯形成反应的加速对于-27mV的偏移Zeta电位而言是标志性的。
因此,本发明的另一个方面是微胶囊,所述微胶囊包括以下项或由以下项组成:
-芯,所述芯包括至少一种疏水的有效成分或由其组成;以及
-胶囊壳,所述胶囊壳包括具有两个或更多个异氰酸酯基团的异氰酸酯,所述异氰酸酯在保护胶体和催化剂的存在下在第一步骤中通过在酸性pH值下反应的胺并且在另外的步骤中通过在碱性pH值下反应的胺进行交联。
出人意料地已经确定,用本发明方法制备的微胶囊具有层状的壳结构或多层的胶囊壳或胶囊壁,所述胶囊壳或胶囊壁由靠近微胶囊芯的由聚氨酯形成的第一层以及在微胶囊外部边缘处的由聚脲形成的第二层构成。
因此,在一个优选的变体中,本发明涉及基于异氰酸酯的微胶囊,其特征在于,所述胶囊壳包括以下项或由以下项组成:由聚氨酯形成的第一层以及由聚脲形成的第二层。
由于所述微胶囊的出色的稳定性和出色的释放能力以及利用本发明微胶囊封装大范围的疏水有效成分的可能性,根据本发明的基于异氰酸酯的微胶囊可以用于关于赋予气味和芳香化的广泛应用领域。
因此,在另一个方面,本发明最后涉及本发明的微胶囊或包括本发明微胶囊的悬浮液用于制备洗涤剂、织物柔软剂、清洁剂、呈液态或固态形式的气味增强剂(香味增强剂)、美妆用品、个人护理产品、农业产品或制药产品的用途。
使用本发明微胶囊的特别适合的使用形式是将其以悬浮液的形式混合到最终产品中。因此,本发明还涉及一种上述微胶囊在液体、尤其在水中的悬浮液。当此类悬浮液被设计为使得微胶囊的重量比例为约20至60重量%、尤其约25至50重量%、更加优选约30至35重量%时,所述悬浮液具有特别有利的特性。
为了防止此类悬浮液分层并且由此实现高储存稳定性,已经证实为有利的是,所述悬浮液具有12至1500mPas的黏度。为了获得所述悬浮液的所希望的黏度,优选使用增稠剂。
本发明的微胶囊特别适合用于包封疏水的香味物质或芳香物质,所述香味物质或芳香物质随后可以用在不同的清洁产品中。
本发明由此尤其还涉及所说明的微胶囊作为洗涤剂、尤其液态洗涤剂、织物柔软剂、清洁剂、呈液态或固态形式的气味增强剂(香味增强剂)、美妆用品、个人护理产品、尤其沐浴露、洗发水、除臭剂和/或身体乳的组成部分的用途。
在上述产品中的微胶囊比例为相对于产品的总重量0.05至15重量%、优选0.2至5重量%。
实施例
借助于下面的实施例详细说明本发明的微胶囊及其有利的特性。
下面详述的稳定性测试在50℃下进行。
实施例1:在带有和没有催化剂(DABCO)、在20至30℃下第一交联剂(赖氨酸盐酸盐)和在35至50℃下进一步交联剂(碳酸胍)的情况下根据本发明方法制备的微胶囊的稳定性数据。作为保护胶体使用了聚乙烯醇。
稳定性测试借助于代表性的软化剂(柔软剂)进行,微胶囊以1重量%的量被加入其中。软化剂随后储存下述时间段。
借助于GS/MS(气相色谱和质谱)分析胶囊内容物。通过与标准物的对比测量确定了胶囊中的香水油含量。例如64%的结果表示,36%的初始加入的香水油量不再存在于胶囊中。
表1
备注:物质:醛、羧酸、酯、伯醇组分在香水油组合物中的比例
香水油4至6的特征在于带有酯、醛和羧酸官能度的组分的高比例。利用本发明的方法对于此类香水油也获得了出色的稳定性数据。
实施例2:根据本发明方法以不同保护胶体制备的微胶囊的稳定性数据:用赖氨酸盐酸盐在5.0的pH值下交联;封装的油:天然CARENδ-3,天然精馏石竹烯,水芹烯L,天然左旋蒎烯α,萜烯γ,异丙基格蓬。
表2
保护胶体 | 3天 | 10天 |
聚乙烯醇 | 83% | 72% |
PVOH的阳离子型铵衍生物 | 69% | 54% |
淀粉 | 80% | 75% |
所有微胶囊显示出出色的稳定性数据。在使用PVOH的铵衍生物时,稳定性略低,这应归因于降低的羟基数量。
实施例3:以香水油4为例减少壳。在内部非水相中的单体(异氰酸酯)含量被降低。
表3
备注:1:20的比率表示,使用5g单体以封装100g香水油。
在10天之后具有>40%的残余油含量的胶囊被认为是稳定的;在此情况下可以将壳减少50%。
实施例4:将根据现有技术的封装工艺和根据本发明方法制备的微胶囊的稳定性进行对比。
如下制备微胶囊:
根据现有技术的封装工艺:交联:仅聚脲网络;催化剂:无;保护胶体:聚乙烯醇;pH值:9。
本发明的方法:由被溶解在香水油加溶剂中的两种异氰酸酯形成的非水相;由聚乙烯醇和DABCO形成的水相;乳化过程:加入在酸性pH值范围内反应的赖氨酸盐酸盐(pH值:4至7);加入在碱性pH值范围内反应的碳酸胍(pH值:7至14);最终胶囊浆料的pH值:5至8。
表4
备注:物质:醛、羧酸、酯、伯醇组分在香水油组合物中的比例
与根据现有技术的封装工艺相比,本发明的封装工艺可以通用,而根据现有技术的工艺在具有高比例的具有酯、醛和羧酸官能度的组分的香水油的情况下在稳定性上有严重损失。本发明的封装工艺尤其在香水油4至6的情况下在稳定性上有增益,而在香水油1至3的情况下稳定性略微降低。
实施例5:形成多层胶囊壳
表5
保护胶体 | 3天,50℃ | 10天,50℃ |
现有技术胶囊 | 77% | 70% |
本发明胶囊,带有PVOH | 70% | 61% |
本发明胶囊,带有PVOH的铵衍生物 | 41% | 33% |
本发明胶囊,带有PVOH的铵衍生物和甘油 | 55% | 49% |
本发明胶囊,带有改性淀粉 | 76% | 67% |
通过使用不同的保护胶体可以证明,利用本发明的方法形成了多层的胶囊壳或胶囊壁。而在所述方法中在没有加入其他羟基的情况下使用了聚乙烯醇(PVOH)的铵衍生物作为保护胶体,胶囊稳定性明显低于在所述方法中附加地加入甘油的情况,由此可以观察到微胶囊的稳定性的提高。通过针对性地去掉羟基(见“本发明胶囊,带有PVOH的铵衍生物”)和针对性地增加羟基(见“本发明胶囊,带有PVOH的铵衍生物和甘油”)可以证明聚氨酯层的形成,聚氨酯层大幅度提高稳定性。
实施例6:本发明微胶囊的感受评估
微胶囊的感受评估如下进行:如在图6中所示,将微胶囊放入柔软剂中然后清洗。对棉和聚酯形成的混合纤维毛巾进行嗅闻。
现有技术的胶囊:10天,50℃,28%香水油。
具有减少的壳的本发明胶囊:10天,50℃,59%香水油。
24名测试人员已经在从1(无气味)至9(非常强的气味)的标度上对清洗后的混合纤维毛巾的香味强度进行评估。
本发明的微胶囊实际上具有与来自现有技术的微胶囊相同的气味。在此优点在于本发明微胶囊的稳定性。本发明微胶囊虽然将相对于香水油将聚合物从1:20减少至1:40,但具有更高的稳定性。
由于上述有利特性,相对于现有技术的微胶囊,长期而言可以预期本发明的微胶囊具有保持不变的品质并因此还具有感受稳定性。来自现有技术的微胶囊在其刚刚制备之后与本发明的微胶囊一样好。但是随着时间推移,它们比本发明微胶囊更快地损失油并且因此闻起来强度较低。
Claims (16)
1.一种用于制备基于异氰酸酯的微胶囊的方法,所述方法包括以下步骤:
(a)提供内部的非水相,所述非水相包括至少一种带有两个或更多个异氰酸酯基团的异氰酸酯或者至少一种带有两个或更多个异硫氰酸酯基团的异硫氰酸酯以及待封装的疏水有效成分;
(b)提供外部的水相,所述水相包括至少一种保护胶体和催化剂;
(c)任选地在稳定剂和/或乳化剂的存在下,将所述内部的非水相和所述外部的水相混合,获得水包油乳液;
(d)通过添加在酸性pH值下反应的胺进行第一交联;
(e)通过添加在碱性pH值下反应的胺进行进一步交联,获得微胶囊;
(f)将在步骤(e)中获得的微胶囊硬化;以及
任选地:
(g)将所述微胶囊从反应溶液中分离并且任选地干燥所述微胶囊。
2.根据权利要求1所述的方法,其中所述具有两个或更多个异氰酸酯基团的异氰酸酯或者所述具有两个或更多个异硫氰酸酯基团的异硫氰酸酯选自由以下项组成的组:脂肪族、环脂肪族、氢化芳香族、芳香族或杂环的多异氰酸酯或多异硫氰酸酯、其取代产物以及上述化合物的混合物。
3.根据前述权利要求1或2之一所述的方法,其中所述至少一种待封装的疏水有效成分选自由以下项组成的组:香味物质、芳香物质、杀生物剂、杀虫剂、选自趋避剂的组的物质、食品添加剂、美妆有效成分、制药有效成分、农业化学品、染料。发光颜料、光学增亮剂、溶剂、蜡、硅酮油、润滑剂,以及上述有效成分的混合物。
4.根据前述权利要求1至3之一所述的方法,其中所述至少一种待封装的疏水有效成分选自由以下项组成的组:具有醛、羧酸或酯官能团的香味物质或芳香物质。
5.根据前述权利要求1至4之一所述的方法,其中所述保护胶体选自由以下项组成的组:二醇,尤其乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、丁二醇异构体、1,2-戊二醇、1,2-己二醇、1,2-辛二醇、1,2-癸二醇、1,2-十二烷二醇,和多元醇,尤其三醇,尤其甘油及其乙氧基化产物和丙氧基化产物,三羟甲基丙烷及其乙氧基化产物和丙氧基化产物,聚乙烯醇(PVOH)及其衍生物,尤其铵官能化或磺酸根官能化的聚乙烯醇,多酚,尤其1,3,5-三羟基苯,淀粉或化学、机械和/或酶改性的淀粉,羧甲基纤维素和聚乙烯基吡咯烷酮,以及上述化合物的混合物。
6.根据前述权利要求1至5之一所述的方法,其中所述保护胶体与淀粉组合使用。
7.根据前述权利要求1至6之一所述的方法,其中所述催化剂为二氮杂二环[2.2.2]辛烷(DABCO)。
8.根据前述权利要求1至7之一所述的方法,其中通过所述在酸性pH值下反应的胺进行的所述第一交联在2至7的pH值下并且任选地在20℃至30℃的温度下进行。
9.根据前述权利要求1至8之一所述的方法,其中所述酸性反应的胺选自由酸性氨基酸盐酸盐、尤其赖氨酸盐酸盐和鸟氨酸盐酸盐组成的组。
10.根据前述权利要求1至9之一所述的方法,其中通过所述碱性反应的胺进行的所述进一步交联在7至14的pH值下并且任选地在35℃至50℃的温度下进行。
11.根据前述权利要求1至10之一所述的方法,其中所述碱性反应的胺选自由二胺、三胺和多元胺以及碳酸胍组成的组。
12.根据前述权利要求1至11之一所述的方法,其中在步骤(f)中所述微胶囊的硬化在55至70℃的温度下进行。
13.根据权利要求1至12中一项或多项获得的微胶囊。
14.基于异氰酸酯的微胶囊,包括以下项或由以下项组成:
-芯,所述芯包括至少一种疏水的有效成分;以及
-胶囊壳,所述胶囊壳包括具有两个或更多个异氰酸酯基团的异氰酸酯,所述异氰酸酯在保护胶体和催化剂的存在下在第一步骤中通过在酸性pH值下反应的胺并且在另外的步骤中通过在碱性pH值下反应的胺进行交联。
15.根据权利要求14所述的基于异氰酸酯的微胶囊,其中所述胶囊壳包括以下项或由以下项组成:由聚氨酯形成的第一层以及由聚脲形成的第二层。
16.根据权利要求13至15之一所述的微胶囊或者由根据权利要求13至15之一所述的微胶囊形成的悬浮液用于制备洗涤剂、织物柔软剂、清洁剂、呈液态或固态形式的气味增强剂(香味增强剂)、美妆用品、个人护理产品、农业产品和制药产品的用途。
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- 2019-02-13 EP EP19705954.6A patent/EP3924102A1/de active Pending
- 2019-02-13 US US17/430,943 patent/US20220105486A1/en active Pending
- 2019-02-13 CN CN201980095136.6A patent/CN113766969A/zh active Pending
- 2019-02-13 WO PCT/EP2019/053600 patent/WO2020164705A1/de unknown
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CN114814065A (zh) * | 2022-04-12 | 2022-07-29 | 上海交通大学 | 幽门螺旋杆菌的唾液中voc标志物及其在制备诊断试剂中的应用 |
CN114814065B (zh) * | 2022-04-12 | 2023-12-01 | 上海交通大学 | 幽门螺旋杆菌的唾液中voc标志物及其在制备诊断试剂中的应用 |
CN114989885A (zh) * | 2022-07-01 | 2022-09-02 | 浙江美之源化妆品有限公司 | 一种三聚氰胺甲醛香水微胶囊的制备方法 |
Also Published As
Publication number | Publication date |
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US20220105486A1 (en) | 2022-04-07 |
WO2020164705A1 (de) | 2020-08-20 |
EP3924102A1 (de) | 2021-12-22 |
JP2022520102A (ja) | 2022-03-28 |
JP7267439B2 (ja) | 2023-05-01 |
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