DK2477595T3 - NOVEL ALDEHYDES AND NITRILES isophorone, AND USE THEREOF IN THE PERFUME PRODUCTION - Google Patents
NOVEL ALDEHYDES AND NITRILES isophorone, AND USE THEREOF IN THE PERFUME PRODUCTION Download PDFInfo
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- DK2477595T3 DK2477595T3 DK10763445.3T DK10763445T DK2477595T3 DK 2477595 T3 DK2477595 T3 DK 2477595T3 DK 10763445 T DK10763445 T DK 10763445T DK 2477595 T3 DK2477595 T3 DK 2477595T3
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- Denmark
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- hydrogen atom
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- 238000004519 manufacturing process Methods 0.000 title claims description 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 title description 10
- 150000001299 aldehydes Chemical class 0.000 title description 7
- 150000002825 nitriles Chemical class 0.000 title description 6
- 239000002304 perfume Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 83
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- -1 alkyl cyanoacetate Chemical compound 0.000 claims description 15
- 239000003205 fragrance Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 230000000873 masking effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
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- 239000006071 cream Substances 0.000 description 9
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical class O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
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- CGZTVBYESYRPON-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)acetonitrile Chemical compound CC1CC(C)(C)CC1CC#N CGZTVBYESYRPON-UHFFFAOYSA-N 0.000 description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- 241000207199 Citrus Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
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- 238000004140 cleaning Methods 0.000 description 5
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- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
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- XGCRJUQYBCDAEW-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)prop-2-enal Chemical compound CC1CC(C)(C)CC1C(=C)C=O XGCRJUQYBCDAEW-UHFFFAOYSA-N 0.000 description 3
- MIGLSAUGGYMUTK-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)propanal Chemical compound O=CC(C)C1CC(C)(C)CC1C MIGLSAUGGYMUTK-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- 244000030166 artemisia Species 0.000 description 1
- 235000009052 artemisia Nutrition 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 229940062650 buchu Drugs 0.000 description 1
- IVLCENBZDYVJPA-ARJAWSKDSA-N cis-Jasmone Natural products C\C=C/CC1=C(C)CCC1=O IVLCENBZDYVJPA-ARJAWSKDSA-N 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- WGPCZPLRVAWXPW-LLVKDONJSA-N gamma-Dodecalactone Natural products CCCCCCCC[C@@H]1CCC(=O)O1 WGPCZPLRVAWXPW-LLVKDONJSA-N 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
- C07C47/11—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0956422A FR2950342B1 (fr) | 2009-09-18 | 2009-09-18 | Nouveaux aldehydes et nitriles issus de l'isophorone, ainsi que leur utilisation en parfumerie |
| PCT/IB2010/054213 WO2011033479A1 (fr) | 2009-09-18 | 2010-09-17 | Nouveaux aldehydes et nitriles issus de l'isophorone, ainsi que leur utilisation en parfumerie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2477595T3 true DK2477595T3 (en) | 2015-10-26 |
Family
ID=41683039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10763445.3T DK2477595T3 (en) | 2009-09-18 | 2010-09-17 | NOVEL ALDEHYDES AND NITRILES isophorone, AND USE THEREOF IN THE PERFUME PRODUCTION |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8592360B2 (https=) |
| EP (1) | EP2477595B1 (https=) |
| JP (1) | JP5856564B2 (https=) |
| CN (1) | CN102573767B (https=) |
| BR (1) | BR112012006108A2 (https=) |
| CA (1) | CA2773226C (https=) |
| DK (1) | DK2477595T3 (https=) |
| ES (1) | ES2549914T3 (https=) |
| FR (1) | FR2950342B1 (https=) |
| IN (1) | IN2012DN02264A (https=) |
| MX (1) | MX2012003326A (https=) |
| PL (1) | PL2477595T3 (https=) |
| PT (1) | PT2477595E (https=) |
| RU (1) | RU2535784C2 (https=) |
| WO (1) | WO2011033479A1 (https=) |
| ZA (1) | ZA201201673B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675074A (zh) * | 2012-05-25 | 2012-09-19 | 江西华士药业有限公司 | 环丙唑醇关键中间体1-(4-氯苯基)-2-环丙基-1-丙酮的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931143A (en) | 1967-02-15 | 1976-01-06 | Pennwalt Corporation | Unsymmetrical aliphatic monoazo compounds |
| US4477683A (en) * | 1982-05-03 | 1984-10-16 | Givaudan Corporation | 3-Methyl-1-(2,3,4-and 2,4,4-trimethyl-1-cyclopentylidene) pent-2-en-4-one and isomers, and perfume compositions thereof |
| DE3345375A1 (de) | 1983-12-15 | 1985-06-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-substituierten but-3-en-l-carbonsaeuren und von deren estern |
| DE3726418A1 (de) * | 1987-08-07 | 1989-02-16 | Dragoco Gerberding Co Gmbh | Verwendung von campholennitrilen als riechstoff |
| DE3928242A1 (de) * | 1989-08-26 | 1991-02-28 | Basf Ag | Cycloalkylidenderivate |
| FR2831165B1 (fr) * | 2001-10-23 | 2005-06-17 | Mane Fils V | Nouveaux derives du norbornane et du norbornene, leur utilisation et produits parfumes les contenant |
-
2009
- 2009-09-18 FR FR0956422A patent/FR2950342B1/fr active Active
-
2010
- 2010-09-17 BR BR112012006108A patent/BR112012006108A2/pt active IP Right Grant
- 2010-09-17 RU RU2012115458/04A patent/RU2535784C2/ru active
- 2010-09-17 US US13/496,783 patent/US8592360B2/en active Active
- 2010-09-17 IN IN2264DEN2012 patent/IN2012DN02264A/en unknown
- 2010-09-17 EP EP10763445.3A patent/EP2477595B1/fr active Active
- 2010-09-17 ES ES10763445.3T patent/ES2549914T3/es active Active
- 2010-09-17 DK DK10763445.3T patent/DK2477595T3/en active
- 2010-09-17 PT PT107634453T patent/PT2477595E/pt unknown
- 2010-09-17 JP JP2012529394A patent/JP5856564B2/ja active Active
- 2010-09-17 PL PL10763445T patent/PL2477595T3/pl unknown
- 2010-09-17 MX MX2012003326A patent/MX2012003326A/es active IP Right Grant
- 2010-09-17 WO PCT/IB2010/054213 patent/WO2011033479A1/fr not_active Ceased
- 2010-09-17 CA CA2773226A patent/CA2773226C/fr active Active
- 2010-09-17 CN CN201080041627.1A patent/CN102573767B/zh active Active
-
2012
- 2012-03-07 ZA ZA2012/01673A patent/ZA201201673B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013505229A (ja) | 2013-02-14 |
| BR112012006108A2 (pt) | 2016-06-07 |
| IN2012DN02264A (https=) | 2015-08-21 |
| US8592360B2 (en) | 2013-11-26 |
| CN102573767B (zh) | 2014-02-26 |
| JP5856564B2 (ja) | 2016-02-10 |
| US20120238486A1 (en) | 2012-09-20 |
| PL2477595T3 (pl) | 2016-01-29 |
| RU2535784C2 (ru) | 2014-12-20 |
| ES2549914T3 (es) | 2015-11-03 |
| WO2011033479A1 (fr) | 2011-03-24 |
| CN102573767A (zh) | 2012-07-11 |
| EP2477595A1 (fr) | 2012-07-25 |
| CA2773226A1 (fr) | 2011-03-24 |
| RU2012115458A (ru) | 2013-10-27 |
| HK1169947A1 (zh) | 2013-02-15 |
| MX2012003326A (es) | 2012-04-30 |
| PT2477595E (pt) | 2015-11-02 |
| ZA201201673B (en) | 2012-10-31 |
| EP2477595B1 (fr) | 2015-07-22 |
| FR2950342B1 (fr) | 2011-09-02 |
| FR2950342A1 (fr) | 2011-03-25 |
| CA2773226C (fr) | 2017-10-31 |
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