EP2938317A1 - Verfahren zur herstellung einer öl-in-wasser-emulsion aus einem öliger wirkstoff für kosmetische, nahrungsmittel- oder pharmazeutische verwendung - Google Patents
Verfahren zur herstellung einer öl-in-wasser-emulsion aus einem öliger wirkstoff für kosmetische, nahrungsmittel- oder pharmazeutische verwendungInfo
- Publication number
- EP2938317A1 EP2938317A1 EP12813375.8A EP12813375A EP2938317A1 EP 2938317 A1 EP2938317 A1 EP 2938317A1 EP 12813375 A EP12813375 A EP 12813375A EP 2938317 A1 EP2938317 A1 EP 2938317A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- emulsion
- oily
- mixture
- less
- active substance
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000013543 active substance Substances 0.000 title claims abstract description 14
- 239000002537 cosmetic Substances 0.000 title claims description 10
- 235000013305 food Nutrition 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000007764 o/w emulsion Substances 0.000 title 1
- 239000000839 emulsion Substances 0.000 claims abstract description 31
- 238000000265 homogenisation Methods 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 4
- 229930185210 Saponoside Natural products 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000007957 coemulsifier Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 4
- 239000001397 quillaja saponaria molina bark Substances 0.000 abstract 1
- 229930182490 saponin Natural products 0.000 abstract 1
- 150000007949 saponins Chemical class 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000002989 Euphorbia neriifolia Species 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000010478 argan oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
- A23D7/04—Working-up
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
- A61K2800/33—Free of surfactant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/81—Preparation or application process involves irradiation
Definitions
- the present invention relates to aqueous emulsions of oily active substances for the cosmetic, food and pharmaceutical industries.
- Cyclodextrin technology is another possible route, but it also has several constraints that severely limit its use.
- saponosides which are plant emulsifiers belonging to the family of carbohydrates (glycosides).
- a first category of applications uses auxiliary substances (carbohydrates, ethanol, ). significant quantities that denature the final emulsion.
- a second mode of application does not use auxiliary substances, as has the patent FR 02 14436, but it does not practically exceed substantially, with a fluidity and stability satisfactory, an oily phase concentration of 30% of the emulsion, which is a troublesome limitation, in particular for certain cosmetic applications.
- No known method to date allows to make fluid and stable aqueous emulsions containing more than 40% oily phase, with less than 1% of vegetable emulsifier. 3. Description of the invention
- the invention relates to a method for manufacturing an aqueous emulsion.
- an oily active substance for cosmetic, food or pharmaceutical application comprising the following steps:
- mixture of hydrophilic components comprising water, an emulsifying saponoside, which represents less than 1% of the emulsion whatever the proportion of oily phase
- a mixture of lipophilic components comprising the oily active substance, which can reach 40% of the emulsion
- At least one hydrophilic additive is added to the mixture of hydrophilic components, and at least one lipophilic additive to the mixture of lipophilic components.
- additives means additional substances such as preservatives, antioxidants, sequestering agents, etc. , ensuring the preservation of the active substance.
- any other means of preservation may be used, for example a sterilization step of the whole of the homogenized emulsion.
- the emulsions obtained are always milky.
- the emulsions of the invention very fluid, can be used as a basis for the production of gels or creams by adding thickeners (s) suitable for application.
- the components of the emulsion, and their% mass, are as follows.
- the hydrophilic components and the lipophilic components are mixed separately to obtain homogeneous phases.
- Homogenization No. 1 of the two phases is carried out with a mixer of the protected trademark Ultra-Turrax, of the rotor-stator type, at 20,000 revolutions / minute.
- Homogenization No. 2 of the preceding mixture is carried out with a high-pressure homogenizer of the protected trademark APV, in recycling, with an operating pressure of 600 bars. A milky and stable milky emulsion is obtained.
- the homogenization times must be determined experimentally and depend on the nature of the vegetable oils and the characteristics of the homogenizers.
- Blend b Sunflower oil 25% + Shea olein 35% + Argan oil 40% Minimum time of homogenization
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Colloid Chemistry (AREA)
- Medicinal Preparation (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20160233.1A EP3708143A1 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
| EP24199286.6A EP4450058A2 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2012/076948 WO2014101941A1 (fr) | 2012-12-27 | 2012-12-27 | Procede de fabrication d'une emulsion aqueuse d'une substance active huileuse pour application cosmetique, alimentaire ou pharmaceutique |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP24199286.6A Division EP4450058A2 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
| EP20160233.1A Division EP3708143A1 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2938317A1 true EP2938317A1 (de) | 2015-11-04 |
Family
ID=47553032
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP24199286.6A Pending EP4450058A2 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
| EP20160233.1A Pending EP3708143A1 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
| EP12813375.8A Ceased EP2938317A1 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer öl-in-wasser-emulsion aus einem öliger wirkstoff für kosmetische, nahrungsmittel- oder pharmazeutische verwendung |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP24199286.6A Pending EP4450058A2 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
| EP20160233.1A Pending EP3708143A1 (de) | 2012-12-27 | 2012-12-27 | Verfahren zur herstellung einer wässrigen emulsion eines ölhaltigen wirkstoffs zur kosmetischen, lebensmittel- oder pharmazeutischen anwendung |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US11000046B2 (de) |
| EP (3) | EP4450058A2 (de) |
| CN (1) | CN104981231B (de) |
| WO (1) | WO2014101941A1 (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR201609395A2 (tr) * | 2016-07-01 | 2018-01-22 | Bioarge Bitkisel Kozmetik Arastirma Gelistirme Muehendislik Ltd Sti | İyileştirilmiş yağ dispersiyonu ve transdermal dağıtımı. |
| US11708258B2 (en) * | 2020-10-24 | 2023-07-25 | Gavin Hazen | Beverage product amendment apparatus and method of use thereof |
| KR102299279B1 (ko) * | 2020-10-28 | 2021-09-08 | (주)아모레퍼시픽 | 나노 에멀젼 화장료 조성물 및 이의 제조 방법 |
| FR3115992B1 (fr) * | 2020-11-06 | 2023-04-21 | Oreal | Composition sous forme d'émulsion comprenant des saponines et une huile végétale |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2740335B1 (fr) * | 1995-10-26 | 1997-12-19 | Oreal | Utilisation de sel de lanthanide, de lithium, d'etain, de zinc, de manganese ou d'yttrium comme antagoniste de substance p |
| JP4549625B2 (ja) * | 2002-01-05 | 2010-09-22 | 株式會社アモーレパシフィック | 人参サポニン代謝産物を有効成分とする微細乳化粒子及びその製造方法、並びにこれを含有する皮膚老化防止用の化粧料組成物 |
| FR2847163B1 (fr) | 2002-11-19 | 2006-07-28 | Jean Claude Epiphani | Procede d'hydrosolubilisation d'un parfum et solution obtenue par le procede |
| PL1613346T3 (pl) * | 2003-04-04 | 2013-03-29 | Zoetis Services Llc | Poddane mikrofluidyzacji emulsje typu olej w wodzie i kompozycje szczepionek |
| US20080107777A1 (en) * | 2006-09-29 | 2008-05-08 | Conopco Inc, D/B/A Unilever | Process for production of compounds, which are starch containing particles coated, embedded or encapsulated by at least one biopolymers |
| WO2010121082A2 (en) | 2009-04-15 | 2010-10-21 | Oxygen Biotherapeutics, Inc. | Emulsions of perfluorocarbons |
| FR2945936A1 (fr) * | 2009-05-26 | 2010-12-03 | Jean Claude Epiphani | Procede de fabrication d'une emulsion aqueuse d'une substance active huileuse pour application cosmetique, alimentaire ou pharmaceutique |
| BR112012013426B8 (pt) | 2009-12-03 | 2021-05-25 | Novartis Ag | métodos para a fabricação de uma emulsão de óleo-em-água, para preparar uma composição de vacina e para preparar um kit de vacina |
| EP2359698B1 (de) * | 2010-01-22 | 2013-12-04 | Symrise AG | Zusammensetzungen mit einem Tensidsystem mit Saponinen und Lecithin |
| DE102010023421A1 (de) * | 2010-06-11 | 2011-12-15 | Sensient Food Colors Germany Gmbh | Farbstoff-Emulsion |
| FR2973227B1 (fr) * | 2011-04-01 | 2014-08-08 | Oreal | Composition cosmetique comprenant du 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one |
| GB201204377D0 (en) * | 2012-03-13 | 2012-04-25 | Givaudan Sa | Composition |
-
2012
- 2012-12-27 EP EP24199286.6A patent/EP4450058A2/de active Pending
- 2012-12-27 EP EP20160233.1A patent/EP3708143A1/de active Pending
- 2012-12-27 WO PCT/EP2012/076948 patent/WO2014101941A1/fr active Application Filing
- 2012-12-27 CN CN201280078006.XA patent/CN104981231B/zh active Active
- 2012-12-27 EP EP12813375.8A patent/EP2938317A1/de not_active Ceased
- 2012-12-27 US US14/653,834 patent/US11000046B2/en active Active
Non-Patent Citations (2)
| Title |
|---|
| None * |
| See also references of WO2014101941A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US11000046B2 (en) | 2021-05-11 |
| WO2014101941A1 (fr) | 2014-07-03 |
| CN104981231B (zh) | 2018-01-30 |
| EP4450058A2 (de) | 2024-10-23 |
| US20150327566A1 (en) | 2015-11-19 |
| CN104981231A (zh) | 2015-10-14 |
| EP3708143A1 (de) | 2020-09-16 |
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