CN102112010A - 风味油乳液 - Google Patents
风味油乳液 Download PDFInfo
- Publication number
- CN102112010A CN102112010A CN2009801305409A CN200980130540A CN102112010A CN 102112010 A CN102112010 A CN 102112010A CN 2009801305409 A CN2009801305409 A CN 2009801305409A CN 200980130540 A CN200980130540 A CN 200980130540A CN 102112010 A CN102112010 A CN 102112010A
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- local flavor
- beverage
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- water
- oil
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- 239000000839 emulsion Substances 0.000 title claims abstract description 57
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 55
- 235000019634 flavors Nutrition 0.000 title claims abstract description 51
- 229920003086 cellulose ether Polymers 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000013361 beverage Nutrition 0.000 claims description 52
- 239000003921 oil Substances 0.000 claims description 24
- 235000019198 oils Nutrition 0.000 claims description 24
- 244000215068 Acacia senegal Species 0.000 claims description 13
- 229920000084 Gum arabic Polymers 0.000 claims description 13
- 239000000205 acacia gum Substances 0.000 claims description 13
- 235000010489 acacia gum Nutrition 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 4
- 239000001525 mentha piperita l. herb oil Substances 0.000 claims description 4
- 235000019477 peppermint oil Nutrition 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- BYXCFUMGEBZDDI-UHFFFAOYSA-N 1,3,7-trimethyluric acid Chemical compound CN1C(=O)N(C)C(=O)C2=C1NC(=O)N2C BYXCFUMGEBZDDI-UHFFFAOYSA-N 0.000 claims description 2
- QHXDTLYEHWXDSO-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(Cl)=NC(N(CC)CC)=N1 QHXDTLYEHWXDSO-UHFFFAOYSA-N 0.000 claims description 2
- 240000000972 Agathis dammara Species 0.000 claims description 2
- 239000001842 Brominated vegetable oil Substances 0.000 claims description 2
- 241000207199 Citrus Species 0.000 claims description 2
- 235000019499 Citrus oil Nutrition 0.000 claims description 2
- 229920002871 Dammar gum Polymers 0.000 claims description 2
- 240000001238 Gaultheria procumbens Species 0.000 claims description 2
- 235000007297 Gaultheria procumbens Nutrition 0.000 claims description 2
- HIZCTWCPHWUPFU-UHFFFAOYSA-N Glycerol tribenzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(OC(=O)C=1C=CC=CC=1)COC(=O)C1=CC=CC=C1 HIZCTWCPHWUPFU-UHFFFAOYSA-N 0.000 claims description 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 2
- 235000019323 brominated vegetable oil Nutrition 0.000 claims description 2
- 239000010630 cinnamon oil Substances 0.000 claims description 2
- 235000020971 citrus fruits Nutrition 0.000 claims description 2
- 239000010500 citrus oil Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- 239000001944 prunus armeniaca kernel oil Substances 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 239000008371 vanilla flavor Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229920003091 Methocel™ Polymers 0.000 description 24
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 239000003381 stabilizer Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 235000015165 citric acid Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003595 mist Substances 0.000 description 6
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 6
- 239000004299 sodium benzoate Substances 0.000 description 6
- 235000010234 sodium benzoate Nutrition 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000015203 fruit juice Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920003107 Methocel™ A15C Polymers 0.000 description 2
- 229920003106 Methocel™ A4C Polymers 0.000 description 2
- 229920003108 Methocel™ A4M Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000012174 carbonated soft drink Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000014058 juice drink Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000011496 sports drink Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 1
- 240000000912 Macadamia tetraphylla Species 0.000 description 1
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 1
- 244000024873 Mentha crispa Species 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000004311 natamycin Substances 0.000 description 1
- 235000010298 natamycin Nutrition 0.000 description 1
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 description 1
- 229960003255 natamycin Drugs 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 210000000051 wattle Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/105—Natural spices, flavouring agents or condiments; Extracts thereof obtained from liliaceae, e.g. onions, garlic
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
- A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/80—Emulsions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Non-Alcoholic Beverages (AREA)
- Seasonings (AREA)
- Colloid Chemistry (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Abstract
本发明描述风味油乳液,所述风味油乳液包含至少一种风味油和水溶性纤维素醚,所述水溶性纤维素醚以足以制备稳定乳液的量存在。
Description
相关申请的交叉引用
本申请要求于2008年8月7日提交的美国临时申请61/086,926的权益。
领域
本申请涉及饮料加工及配方。
背景
许多饮料,包括碳酸软饮品、非碳酸果汁饮品、运动饮品和果汁,结合风味油(flavor oil)以向饮料赋予风味,并且在一些情况下为外观性质。典型地,通过将较大量的水性部分与含有风味油的乳液浓缩物结合而形成饮料。除了风味油以外,乳液浓缩物通常含有水、防腐剂、酸化剂、增重剂、以及保持乳液随时间变化均匀的稳定剂(水胶体)。非常重要的是稳定剂防止乳液以及稀释后的最终饮料的分离。不是所有稳定剂都同样地起到良好的作用,原因在于稳定剂必须在乳液的低pH条件和饮料的相对较高的pH条件下都是有效的。此外,稳定剂必须对消费而言是安全的。
数年来,阿拉伯树胶已经成为工业中优选的稳定剂。然而,阿拉伯树胶受困于若干缺点,包括不稳定的供给。阿拉伯树胶来自所谓“树胶地带(gum belt)”非洲国家如经历了干旱和国内动荡的乍得(Chad)、苏丹、尼日尔和塞内加尔中的金合欢树。因此,需要具有与阿拉伯树胶相当性能的稳定剂用于风味油乳液。
概述
在一个实施方案中,本发明提供风味油乳液,所述风味油乳液包含至少一种风味油和水溶性纤维素醚,所述水溶性纤维素醚以足以制备稳定乳液的量存在。
说明
在一个实施方案中,本发明提供了风味油乳液,所述风味油乳液包含至少一种风味油和以足以制备稳定乳液的量存在的水溶性纤维素醚。“稳定乳液”是不分离的乳液,即,不能观察到水汇集在乳液的下部、或是油形成于乳液的上部。不是所有的水溶性纤维素醚都形成稳定乳液,并且不打算通过后附权利要求涵盖不形成稳定乳液的那些水溶性纤维素醚。在一个实施方案中,乳液保持稳定达至少30天、优选至少60天、更优选至少90天、最优选至少120天。
虽然不是关键的特性,但是存在即使经历极端粘度下降仍然保持稳定的乳液,在一个实施方案中,乳液在至少120天期间经历小于5%,优选小于2%,更优选小于1%的粘度降低。
在优选的实施方案中,水溶性纤维素醚是甲基纤维素或羟丙基甲基纤维素中的至少一种。在一个实施方案中,水溶性纤维素醚选自在25℃、在水中的2%溶液的布鲁克菲尔德粘度(Brookfield viscosity)小于约4000cps,优选小于约1000cps的那些水溶性纤维素醚。在优选的实施方案中,水溶性纤维素醚选自布鲁克菲尔德粘度优选小于约150cps,优选小于约100cps,更优选小于约25cps的那些水溶性纤维素醚。
在一个实施方案中,水溶性纤维素醚是具有约15至约25的MS和约5至约15的DS的羟丙基甲基纤维素。
在一个实施方案中,水溶性纤维素醚可以以商品名METHOCEL K3商购自陶氏化学公司(The Dow Chemical Company)。在一个实施方案中,水溶性纤维素醚可以以商品名METHOCEL A15 FG公开地获自陶氏化学公司(The Dow Chemical Company)。在一个实施方案中,水溶性纤维素醚可以以商品名METHOCEL SGA 7C FG公开地获自陶氏化学公司(The Dow Chemical Company)。在一个实施方案中,水溶性纤维素醚可以以商品名METHOCEL SGA 150 FG公开地获自陶氏化学公司(The Dow Chemical Company)。
在一个实施方案中,按形成乳液的组合物(emulsion forming composition)的重量计,水溶性纤维素醚以约0.1%至约15%的量、优选以约0.5%至约10%的量、更优选以约1%至约7%的量存在。
风味油可以为任何提供味道、气味或所述两者的可消费疏水性组分。在一个实施方案中,风味油选自柑橘属油;坚果油;咖啡油;可乐油(cola oils);薄荷油,包括绿薄荷油(spearmint)油、冬青油和胡椒薄荷油;以及香料油(spice oils),包括香草油、杏仁油、肉桂油、丁香油和月桂油;或它们的共混物。在一个实施方案中,风味油获自柑橘皮。在一个实施方案中,按形成乳液的组合物的重量计,风味油以约1%至约30%的量、优选以约5%至约15%的量、更优选以约11%至约13%的量存在。
风味油乳液可以包含另外的常规成分,如水、防腐剂、酸化剂或增重剂。防腐剂的实例包括苯甲酸钠、亚硫酸盐类、二氧化硫、亚硝酸盐和硝酸盐、山梨酸、纳他霉素、甘油酯、丙酸和和焦碳酸二乙酯。酸化剂的实例包括柠檬酸、乳酸、苹果酸、己二酸、苯甲酸、富马酸、丙酸、琥珀酸、酒石酸、磷酸和碳酸。在一个实施方案中,增重剂为溴化植物油、酯胶、蔗糖二乙酸六异丁酸酯(sucrose diacetate hexa-isoburtyurate)、精制达玛树脂、干纳巴蜡(ganuaba wax)、苯甲酸苄酯、聚甘油酯或三苯甲酸甘油酯中的至少一种。本领域技术人员易于确定对于获得由任选成分提供的所需性质有效的这种成分的量。
本发明的风味油乳液可以通过传统的乳液形成法制备。
处于相当高浓度(20%以上)的阿拉伯树胶是用于传统乳液的优选稳定剂,原因在于其表面活性性质(来自天然蛋白含量)和良好的酸稳定性。在一个实施方案中,本发明在乳液中提供了阿拉伯树胶的至少部分替代物(replacement)。因而在一个实施方案中,风味油乳液含有小于约10%、优选小于约7%、优选小于约5%、优选小于约3%、优选小于约1%、更优选小于约0.1%、最优选小于0.0001%的阿拉伯树胶。
在一个实施方案中,可以将本发明的风味油乳液与较大量的水性部分结合而形成饮料,例如碳酸软饮品、非碳酸果汁饮品、柑橘风味的饮品、运动饮品或果汁,只要饮料加工温度低于水溶性纤维素醚的热凝胶化(thermogelation)温度即可。因而,在一个实施方案中,饮料是在环境温度加工的。
风味油有助于在完成的饮料中获得浊度、赋予天然果汁形象或外观。浑浊由精油小滴在完成的饮料的水相中的微细分布而产生。然而,由于在调味用油(<0.9g/ml)和完成的水性饮料(>1.00g/ml)之间的比重的不相容性,可能出现稳定性问题如分离,证据为容器颈部周围的脂肪环效果(fatty ringing effect)或容器底部的清液。希望的是饮料不表现出任何分离。在一个实施方案中,饮料保持稳定达至少200天。
实施例
以下实施例仅用于示例的目的并且不意为限制本发明的范围。作为参考,水溶性纤维素醚大致具有表1中描述的25℃时在水中的2%溶液的布鲁克菲尔德粘度。
表1
粘度(eps) | |
METHOCEL A15 FG纤维素醚 | 15 |
METHOCEL SGA 150 FG纤维素醚 | 150 |
METHOCEL A4C FG纤维素醚 | 400 |
METHOCEL SGA7C FG纤维素醚 | 700 |
METHOCEL A15C FG纤维素醚 | 1500 |
METHOCEL A4M FG纤维素醚 | 4000 |
METHOCEL SGA16M FG纤维素醚 | 16000 |
METHOCEL SGA50M FG纤维素醚 | 50000 |
实施例1
根据本发明的示例性风味油乳液含有表1A和1B中列举的组分。
表1A
表1B
用于表1A和1B的单位是重量百分数。表1A中纤维素醚的量(具有12%风味油)被选择为具有250-450cps的目标配方粘度。表1B中纤维素醚的量(具有8%风味油)被选择为具有25-80cps的目标配方粘度。
将酯胶溶解在橙油中进行配制。分别地,将柠檬酸、苯甲酸钠和纤维素醚干混。随后将此干混物加到油中,并混合以形成均匀的浆液。将水(65°F)加到该浆液中,用Silverson混合器以1200rpm混合约3min以形成预制乳液。随后用MICROFLUIDICS匀质器以3000psi将所述预制乳液均匀化。
实施例2
根据本发明的示例性风味油乳液含有表2A&2B中列举的组分。
表2A
第11批 | 第12批 | 第13批 | 第14批 | |
METHOCEL A15纤维素醚 | 3 | -- | -- | -- |
METHOCEL A4C纤维素醚 | -- | 1 | -- | -- |
METHOCEL A15C纤维素醚 | -- | -- | 0.8 | -- |
METHOCEL A4M纤维素醚 | -- | -- | -- | 0.6 |
橙油 | 12 | 12 | 12 | 12 |
酯胶 | 5 | 5 | 5 | 5 |
柠檬酸 | 0.15 | 0.15 | 0.15 | 0.15 |
苯甲酸钠 | 0.02 | 0.02 | 0.02 | 0.02 |
水 | QC | QC | QC | QC |
表2B
第15批 | 第16批 | 第17批 | 第18批 | 第19批 | |
METHOCEL A15纤维素醚 | -- | -- | -- | -- | 1.5 |
METHOCEL SGA 150纤维素醚 | 1.05 | -- | -- | -- | 0.5 |
METHOCEL SGA 7C纤维素醚 | -- | 0.875 | -- | -- | -- |
METHOCEL SGA 16M纤维素醚 | -- | -- | 0.6 | -- | -- |
METHOCEL SGA 50M纤维素醚 | -- | -- | -- | 0.5 | -- |
橙油 | 12 | 12 | 12 | 12 | 12 |
酯胶 | 5 | 5 | 5 | 5 | 5 |
柠檬酸 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
苯甲酸钠 | 0.02 | 0.02 | 0.02 | 0.02 | 0.02 |
水 | QC | QC | QC | QC | QC |
可以根据实施例1中描述的方案制备这些批次。
实施例3(比较)
比较组合物含有表3中列举的组分。
表3
比较批次A | 比较批次B | |
阿拉伯树胶 | 20 | 15 |
橙油 | 12 | 8 |
酯胶 | 5 | 5 |
柠檬酸 | 0.15 | 0.15 |
苯甲酸钠 | 0.02 | 0.02 |
水 | QC | QC |
将批次A和B中的阿拉伯树胶的量选择为分别具有250-450cps和25-80cps的目标配方粘度。如上,将酯胶溶解在橙油中进行配制。分别地,将柠檬酸、苯甲酸钠和阿拉伯树胶干混。随后将此干混物加到油中,并混合以形成均匀的浆液。将水(65°F)加到该浆液中,用Silverson混合器以1200rpm混合约3min以形成预制乳液。随后用MICROFLUIDICS匀质器以3000psi将所述预制乳液均匀化。
实施例4
制成基本上按照以上实施例1和3中描述的方案制备的乳液并列举在表4中。
表4
初始乳液粘度 | 120天乳液粘度 | 粘度损失% | 120天pH | 120天分离 | |
第1批 | 303 | 193 | 36 | 3.2 | 显著 |
第6批 | 43 | 36 | 16 | 3.15 | 显著 |
第2批 | 324 | 96 | 70 | 3.18 | 显著 |
第7批 | 45 | 26 | 42 | 3.09 | 显著 |
第3批 | 424 | 403 | 5 | 3.27 | 轻微 |
第8批 | 75.5 | 50 | 34 | 3.27 | 轻微 |
第4批 | 690 | 204 | 70 | 3.16 | 轻微 |
第9批 | 27.5 | 16 | 42 | 3.15 | 轻微 |
第5批 | 164 | 147 | 10 | 3.43 | 无 |
第10批 | 30 | 36 | N/A | 3.24 | 无 |
比较批次A | 250 | 319 | N/A | 4.19 | 轻微 |
比较批次B | 60 | 72 | N/A | 4.13 | 无 |
全部乳液最初都是稳定的。在后均匀化后确定乳液的粘度,将乳液转移至玻璃缸中,并于室温(~70°F)储存在试验台上。4个月后,确定最终粘度以及分离的可见观察。
实施例5
制成基本上按照以上实施例2和3中描述的方案制备的乳液并列举在表5中。
表5
初始乳液粘度 | 30天乳液粘度 | 粘度损失% | 30天分离 | |
第11批 | 240 | 275 | N/A | 无 |
第12批 | 198 | 120 | 39.39 | 显著 |
第13批 | 188 | 114 | 39.36 | 显著 |
第14批 | 142 | 64 | 54.93 | 显著 |
第15批 | 204 | 218 | N/A | 无 |
第16批 | 185 | 103 | 44.32 | 无 |
第17批 | 174 | 27 | 84.48 | 轻微 |
第18批 | 185 | 24 | 87.03 | 显著 |
第19批 | 230 | 未确定 | 未确定 | 无 |
比较批次A | 270 | 367 | N/A | 无 |
全部乳液最初都是稳定的。在后均匀化后确定乳液的粘度,将乳液转移至玻璃缸中,并于室温(~70°F)储存在试验台上。1个月后,确定30天粘度以及分离的可见观察。
第11批(含有低粘度METHOCEL A15)提供了优异的乳液稳定性。因为所用METHOCEL纤维素的粘度增加(4C、15C和4M级),所以相应的乳液批次(12、13和14)在30天后不稳定。
第15和16批(含有METHOCEL SGA150和SGA7C)提供了良好的乳液稳定性。因为所用METHOCEL纤维素的粘度增加(SGA16M和SGA50M级),所以相应的乳液批次(17和18)在30天后不稳定。
第19批含有METHOCEL A15和METHOCEL SGA150的共混物,并且在30天内显示出优异的稳定性。
含有阿拉伯树胶的比较批次A也显示出良好的乳液稳定性。
实施例6
根据本发明的饮料和比较例含有表6中列举的组分。
表6
将除了乳液以外的所有组分在环境温度合并。随后加入乳液并使用汤匙等混合约1分钟。
实施例7
根据本发明的饮料和比较例含有表7中列举的组分。
表7
可以根据实施例6中描述的方案制备饮料。
实施例8
制成基本上按照以上实施例6中描述的方案制备的饮料并列举在表8中。
表8
在一周的生产中使用风味剂乳液(flavor emulsion)制备饮料。饮料随时间保持适当的浑浊效果的能力通过使用Nippon Senshoku COH-300A颜色-油-雾度(Color-Oil-Haze)测量装置测量浊度(%雾度和/或mg/L固体)来估定。将样品装填在80ml样品池中并对照空白池测量光透射/散射。虽然含有Methocel K3的风味剂乳液在7个月后显示出良好的稳定性,但是相应饮料(饮料5)配方的不透明性显著降低并且是不可接受的。另一方面,Methocel A15、Methocel SGA 150和阿拉伯树胶对风味剂乳液(第3、4批和比较批次A)提供了可接受的稳定性和可接受的浑浊效果(饮料3,4和比较饮料A)。
实施例9
制成基本上按照以上实施例7中描述的方案制备的饮料并列举在表9中。
表9
初始雾度 | 30天储存后的雾度 | 30天储存后的稳定性 |
饮料6 | 87.76 | 70.46 | 是 |
饮料7 | 91.04 | 87.18 | 否 |
饮料8 | 91.26 | 87.65 | 否 |
饮料9 | 90.69 | 84.42 | 否 |
饮料10 | 91.11 | 87.21 | 是 |
饮料11 | 91.27 | 87.36 | 是 |
饮料12 | 91.29 | 87.79 | 否 |
饮料13 | 91.25 | 88.61 | 否 |
饮料14 | 91.38 | -- | 是 |
比较饮料A | 91.2 | 88.21 | 是 |
在一星期的生产内使用风味剂乳液制备饮料。确定这些批次的初始雾度、30天后的雾度、饮料稳定性和视觉可接受的不透明性。在1个月的储存后,全部饮料样品都具有可接受的视觉浑浊效果。浑浊可能与小滴聚结有关,但是不完全与饮料稳定性相关联。饮料稳定性看来遵循乳液稳定性。
应理解的是,本发明不限于在本文中具体公开和示例的实施方案。本发明的各种改良对于本领域技术人员将是明显的。可以在不偏离后附权利要求的范围的条件下做出这样的改变和改良。
此外,每个列举的范围都包括范围的全部组合和次组合(subcombination),以及其中包含的具体数字。另外,在此说明书中引用或描述的每篇文件的公开内容都特此通过引用其全文结合在本文中。
Claims (18)
1.一种风味油乳液,所述风味油乳液包含:
至少一种风味油;和
水溶性纤维素醚,所述水溶性纤维素醚以足以制备稳定乳液的量存在。
2.根据权利要求1所述的风味油乳液,其中所述风味油选自柑橘属油;咖啡油;可乐油;薄荷油,包括绿薄荷油、冬青油和胡椒薄荷油;以及香料油,包括香草油、杏仁油、肉桂油、丁香油和月桂油;或它们的共混物。
3.根据权利要求1所述的风味油乳液,其中按形成乳液的组合物的重量计,所述风味油以约1%至约30%的量,优选以约5%至约15%的量,更优选以约11%至约13%的量存在。
4.根据权利要求1所述的风味油乳液,其中所述乳液保持稳定至少30天,优选至少60天,更优选至少90天,最优选至少120天。
5.根据权利要求1所述的风味油乳液,其中所述乳液在至少120天期间经历小于5%,优选小于2%,更优选小于1%的粘度降低。
6.根据权利要求1所述的风味油乳液,其中所述水溶性纤维素醚是甲基纤维素或羟丙基甲基纤维素中的至少一种。
7.根据权利要求6所述的风味油乳液,其中所述水溶性纤维素醚选自在25℃、在水中的2%溶液的布鲁克菲尔德粘度小于约4000cps,优选小于约1000cps,优选小于约150cps,优选小于约100cps,更优选小于约25cps的那些水溶性纤维素醚。
8.根据权利要求6所述的风味油乳液,其中所述水溶性纤维素醚是具有约15至约25的MS和约5至约15的DS的羟丙基甲基纤维素。
9.根据权利要求1所述的风味油乳液,其中按形成乳液的组合物的重量计,所述水溶性纤维素醚以约0.1%至约15%的量,优选以约0.5%至约10%的量,更优选以约1%至约7%的量存在。
10.根据权利要求1所述的风味油乳液,所述风味油乳液还包含水、防腐剂、酸化剂或增重剂中的至少一种。
11.根据权利要求10所述的风味油乳液,其中所述增重剂为溴化植物油、酯胶、蔗糖二乙酸六异丁酸酯、精制达玛树脂、干纳巴蜡、苯甲酸苄酯、聚甘油酯或三苯甲酸甘油酯中的至少一种。
12.根据权利要求1所述的风味油乳液,条件是所述风味油乳液含有小于约10%,优选小于约7%,优选小于约5%,优选小于约3%,优选小于约1%,更优选小于约0.1%,最优选小于0.0001%的阿拉伯树胶。
13.从根据权利要求1所述的风味油乳液加工的饮料,条件是所述饮料加工温度低于所述水溶性纤维素醚的热凝胶化温度。
14.根据权利要求13所述的饮料,其中所述饮料是在环境温度加工的。
15.根据权利要求13所述的饮料,其中所述饮料是碳酸饮料。
16.根据权利要求13所述的饮料,其中所述饮料不是碳酸饮料。
17.根据权利要求13所述的饮料,其中所述饮料是柑橘风味的饮料。
18.根据权利要求13所述的饮料,其中所述饮料保持稳定至少200天。
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US8692608P | 2008-08-07 | 2008-08-07 | |
US61/086,926 | 2008-08-07 | ||
PCT/US2009/053079 WO2010017435A1 (en) | 2008-08-07 | 2009-08-07 | Flavor oil emulsions |
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CN102112010A true CN102112010A (zh) | 2011-06-29 |
CN102112010B CN102112010B (zh) | 2013-08-21 |
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CN2009801305409A Expired - Fee Related CN102112010B (zh) | 2008-08-07 | 2009-08-07 | 风味油乳液 |
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US (1) | US20110135801A1 (zh) |
EP (1) | EP2317874B1 (zh) |
JP (1) | JP5744733B2 (zh) |
KR (1) | KR20110052689A (zh) |
CN (1) | CN102112010B (zh) |
BR (1) | BRPI0912061A8 (zh) |
MX (1) | MX2011001386A (zh) |
WO (1) | WO2010017435A1 (zh) |
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JP6975831B2 (ja) * | 2019-10-10 | 2021-12-01 | 三栄源エフ・エフ・アイ株式会社 | 香気保留性向上用組成物、及びその製造方法 |
JP7491504B2 (ja) * | 2019-12-25 | 2024-05-28 | 有限会社ロゴス | 風味油脂組成物の製造方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US2906626A (en) * | 1957-07-22 | 1959-09-29 | Dow Chemical Co | Edible oil emulsions |
US4084012A (en) * | 1975-11-03 | 1978-04-11 | The Dow Chemical Company | Edible oil emulsions |
US5700397A (en) * | 1992-06-16 | 1997-12-23 | Fuji Oil Co., Ltd. | Emulsifier, emulsion composition, and powder composition |
DE102006019241A1 (de) * | 2006-04-24 | 2007-10-25 | Dietmar Härtel | Verwendung einer Proteine und Polysaccharide enthaltenden Emulsion mit hoher Wasserbindung für Lebensmittel, insbesondere Getränke, cremiger Konsistenz und Verfahren zur Herstellung einer solchen Emulsion |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4150122A (en) * | 1978-01-05 | 1979-04-17 | E. I. Du Pont De Nemours And Company | Substituted carbamates |
US5374444A (en) * | 1991-06-28 | 1994-12-20 | Langner; Bruce J. | Fiber beverage and method of manufacture |
AU7261296A (en) * | 1995-10-12 | 1997-04-30 | Mccormick & Company, Inc. | Double encapsulation process and flavorant compositions prepared thereby |
JP2007209288A (ja) * | 2006-02-10 | 2007-08-23 | Sanei Gen Ffi Inc | 乳化型ドレッシング |
-
2009
- 2009-08-07 JP JP2011522257A patent/JP5744733B2/ja not_active Expired - Fee Related
- 2009-08-07 WO PCT/US2009/053079 patent/WO2010017435A1/en active Application Filing
- 2009-08-07 KR KR1020117005223A patent/KR20110052689A/ko not_active Application Discontinuation
- 2009-08-07 CN CN2009801305409A patent/CN102112010B/zh not_active Expired - Fee Related
- 2009-08-07 MX MX2011001386A patent/MX2011001386A/es active IP Right Grant
- 2009-08-07 EP EP09791263.8A patent/EP2317874B1/en not_active Not-in-force
- 2009-08-07 BR BRPI0912061A patent/BRPI0912061A8/pt not_active Application Discontinuation
- 2009-08-07 US US13/057,851 patent/US20110135801A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2906626A (en) * | 1957-07-22 | 1959-09-29 | Dow Chemical Co | Edible oil emulsions |
US4084012A (en) * | 1975-11-03 | 1978-04-11 | The Dow Chemical Company | Edible oil emulsions |
US5700397A (en) * | 1992-06-16 | 1997-12-23 | Fuji Oil Co., Ltd. | Emulsifier, emulsion composition, and powder composition |
DE102006019241A1 (de) * | 2006-04-24 | 2007-10-25 | Dietmar Härtel | Verwendung einer Proteine und Polysaccharide enthaltenden Emulsion mit hoher Wasserbindung für Lebensmittel, insbesondere Getränke, cremiger Konsistenz und Verfahren zur Herstellung einer solchen Emulsion |
Non-Patent Citations (2)
Title |
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HAMED MIRHOSSEINI,ET AL: "Influence of pectin and CMC on physical stability,turbidity loss rate,cloudiness and flavor release of orange beverage emulsion during storage", 《CARBOHYDRATE POLYMERS》 * |
N.SARKAR: "Thermal gelation properties of methyl and hydroxypropyl methylcellulose", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
Also Published As
Publication number | Publication date |
---|---|
WO2010017435A1 (en) | 2010-02-11 |
CN102112010B (zh) | 2013-08-21 |
JP5744733B2 (ja) | 2015-07-08 |
US20110135801A1 (en) | 2011-06-09 |
KR20110052689A (ko) | 2011-05-18 |
BRPI0912061A8 (pt) | 2016-11-22 |
JP2011530292A (ja) | 2011-12-22 |
MX2011001386A (es) | 2011-04-21 |
EP2317874B1 (en) | 2013-04-24 |
BRPI0912061A2 (pt) | 2016-06-14 |
EP2317874A1 (en) | 2011-05-11 |
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