EP2480072A2 - Agents decouplants organiques - Google Patents
Agents decouplants organiquesInfo
- Publication number
- EP2480072A2 EP2480072A2 EP10734753A EP10734753A EP2480072A2 EP 2480072 A2 EP2480072 A2 EP 2480072A2 EP 10734753 A EP10734753 A EP 10734753A EP 10734753 A EP10734753 A EP 10734753A EP 2480072 A2 EP2480072 A2 EP 2480072A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- effective amount
- aqueous system
- decoupling agent
- decoupling
- agent
- 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.)
- Withdrawn
Links
- 239000004061 uncoupling agent Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000001580 bacterial effect Effects 0.000 claims abstract description 17
- 239000002028 Biomass Substances 0.000 claims abstract description 16
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229960003237 betaine Drugs 0.000 claims abstract description 7
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000012141 vanillin Nutrition 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 239000010802 sludge Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 6
- 238000004065 wastewater treatment Methods 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- -1 N-trimethylglycine Chemical compound 0.000 claims description 2
- 239000003295 industrial effluent Substances 0.000 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 3
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000032823 cell division Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 102000006270 Proton Pumps Human genes 0.000 description 1
- 108010083204 Proton Pumps Proteins 0.000 description 1
- 241001647970 Shinella granuli Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- TTWYZDPBDWHJOR-IDIVVRGQSA-L adenosine triphosphate disodium Chemical compound [Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O TTWYZDPBDWHJOR-IDIVVRGQSA-L 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- QTUOYBXDUHAXBB-UHFFFAOYSA-N diphosphanium sulfate Chemical compound [PH4+].[PH4+].[O-]S([O-])(=O)=O QTUOYBXDUHAXBB-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000010627 oxidative phosphorylation Effects 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- RDBMUARQWLPMNW-UHFFFAOYSA-N phosphanylmethanol Chemical compound OCP RDBMUARQWLPMNW-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F3/00—Biological treatment of water, waste water, or sewage
- C02F3/02—Aerobic processes
- C02F3/12—Activated sludge processes
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2305/00—Use of specific compounds during water treatment
- C02F2305/04—Surfactants, used as part of a formulation or alone
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F3/00—Biological treatment of water, waste water, or sewage
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
Definitions
- the invention relates to organic derivatives and their use as decoupling agents.
- the present invention relates to such decoupling agents for use in the regulation of bacterial biomass in aqueous systems, particularly in wastewater treatment plants, as well as the use of such agents and a process use of these agents.
- the decoupling activity of a molecule consists in acting on the bacterial cellular energetics so as to reduce the biomass production of the wastewater while keeping the purifying activity of the bacterial cell by biological degradation of organic molecules.
- This decoupling activity of a molecule is interesting for a treatment plant application, hereinafter abbreviated as STEP, in the case where it makes it possible to reduce the production of activated sludge significantly at the source.
- the production of biomass and thus activated sludge in the treatment of wastewater originates from the consumption of nutrients in the wastewater.
- nutrients are oxidized and this releases energy that can be used by microorganisms as part of cell division.
- the consumption of nutrients induces a proton flux at the level of the bacterial membrane by the phenomenon of oxidative phosphorylation; this flux will establish a proton gradient which itself rotates proton pumps that allow the synthesis of ATP (adenosine triphosphate) from ADP + P at the level of the ATP synthetase enzyme complex.
- ATP provides energy to the cell during cellular processes (including cell division).
- Decoupling is the inhibition of the formation of energy reserves in the form of ATP.
- a decoupling agent decreases the energy efficiency of carbon combustion while increasing the proportion of oxidized carbon to CO2. Decoupling results in lower biomass production and higher oxygen consumption.
- the bacterial biomass produced during wastewater treatment is expensive to eliminate and therefore a decrease in biomass leads to a reduction in disposal costs.
- An object of the present invention is to propose decoupling molecules whose efficiency is measured by a decrease in the production of biological sludge at source, that is to say in the aeration basins of urban wastewater treatment plants. at least 30%.
- Another object of the present invention is to provide uncoupling molecules whose efficiency is substantially equivalent to or even greater than the reference molecule THPS (Tetrakis hydroxymethyl phosphonium) whose effectiveness in reducing the production of biological sludge has been shown in FIG. the patent application WO 2004/1 13236.
- THPS Tetrakis hydroxymethyl phosphonium
- Another aim of the present invention is to propose decoupler molecules that are alternative to THPS, whose abiotic and biotic degradability is less rapid than that of THPS, without the said molecules being non-degradable, which would pose environmental problems.
- Another object of the present invention is to provide decoupling molecules whose toxicological and ecotoxicological profile is satisfactory and in adequacy with their use in STEP. Indeed, these molecules must have a low impact on the environment and ultimately be biodegradable while having a biotic and abiotic degradation allowing them to have a satisfactory reactivity on the bacterial biomass.
- the present invention which indeed relates to a method for regulating the growth of bacterial biomass in an aqueous system comprising adding to the aqueous system, or bringing into contact with the aqueous system, an effective amount of a decoupling agent selected from vanillin, pentaerythritol and a betaine of general formula (1):
- R groups are chosen from a linear or branched alkyl group having 1 to 8 carbon atoms and n is a number between 1 and 5.
- R is a methyl group
- n is 1 and the product of formula (1) is referred to in the literature as trimethylglycine, N-trimethylglycine, glycine betaine or glycine of formula (2):
- the effective amount of decoupling agent added to the aqueous system can be up to 5000 mg / l, for example up to 3000 mg / l, such as up to 1000 mg / l.
- the effective amount of decoupling agent added to the aqueous system is from 0.005 mg / l to 500 mg / l, for example from 0.01 mg / l to 300 mg / l, such as 0.05 mg / l. at 100 mg / l. More preferably, the effective amount of decoupling agent is from 0.1 to 10 mg / l, for example from 0.5 mg / l to 7.5 mg / l, such as from 1 to 5 mg / l.
- the decoupling agent may be formulated with one or more of the following conventionally used chemicals in the treatment of wastewater:
- the aqueous system will be a wastewater treatment plant that is used for the treatment of industrial or municipal effluents.
- This facility recovers wastewater from industrial processes (eg paper production, the food industry, the chemical industry) and / or domestic and institutional buildings and similar facilities, using microorganisms in aerobic, anoxic processes (eg denitrification), to consume organic pollutants and to make water suitable for reuse or release into the environment.
- the present invention therefore provides a method for regulating the growth of bacterial biomass in an aqueous system, which method comprises contacting an effective amount of a decoupling agent as defined above directly with the bacterial biomass. . To implement this method, it is recommended to contact in a limited time a maximum volume of activated sludge with the decoupling agent so as to obtain optimal efficiency thereof.
- the effective amount of decoupling agent can be from 0.1 to 1000 milligrams per gram of solids present in the sludge (expressed as dry matter) in the aqueous system, preferably from 0.5 to 750 mg / g, by from 1 to 500 mg / g, such as from 5 to 100 mg / g.
- Oxitop® bottle respirometry is used.
- Bacterial strains known and representative of the activated sludge (because isolated in aeration tanks) are inoculated in a culture medium in the presence of a certain concentration of the decoupling agent over a period of 7 days.
- the comparison of the respiration of inocula treated compared to controls (inocula untreated) can measure the overconsumption of oxygen, physiological signature of the decoupling effect on bacteria.
- THPS tetrakis (hydromethyl) phosphonium sulfate
- Vanillin shows an effectiveness from 0.5 ppm up to 20 ppm.
- Pentaerythritol shows an efficiency in screening test in concentration ranges between 2 and 20 ppm with a significant decoupling factor because close to 20%.
- Glycine betaine has optimal efficacy in the concentration range 2 to 8ppm.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biodiversity & Conservation Biology (AREA)
- Microbiology (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0904509A FR2950226B1 (fr) | 2009-09-22 | 2009-09-22 | Agents decouplants organiques |
| PCT/EP2010/060792 WO2011035949A2 (fr) | 2009-09-22 | 2010-07-26 | Agents decouplants organiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2480072A2 true EP2480072A2 (fr) | 2012-08-01 |
Family
ID=42072938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP10734753A Withdrawn EP2480072A2 (fr) | 2009-09-22 | 2010-07-26 | Agents decouplants organiques |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20130005810A1 (fr) |
| EP (1) | EP2480072A2 (fr) |
| JP (1) | JP2013505277A (fr) |
| KR (1) | KR20120101349A (fr) |
| CN (1) | CN102711457A (fr) |
| FR (1) | FR2950226B1 (fr) |
| WO (1) | WO2011035949A2 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107739103A (zh) * | 2017-10-24 | 2018-02-27 | 沈阳建筑大学 | 一种复合解偶联剂及其制备方法 |
| CN119038737A (zh) * | 2024-08-27 | 2024-11-29 | 上海城投污水处理有限公司 | 一种同步抑制活性污泥丝状菌膨胀和粘性膨胀的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2178960B (en) * | 1985-08-06 | 1990-03-21 | Albright & Wilson | Novel biocidal mixture |
| RU2323746C2 (ru) * | 2003-06-20 | 2008-05-10 | РОДИА ЮКей ЛИМИТЕД | Разобщающие агенты |
| JP2006305552A (ja) * | 2005-03-30 | 2006-11-09 | Kurita Water Ind Ltd | 糸状性バルキングの抑制方法及び抑制剤 |
| AU2005333269A1 (en) * | 2005-03-31 | 2006-12-28 | Bioneutral Laboratories Corporation Usa | Compositions for treating and removing noxious materials malodors and microbes, and methods of use and preparation thereof |
| KR20080103090A (ko) * | 2006-03-10 | 2008-11-26 | 유조 츠치다 | 항미생물제 및 항미생물성 조성물 |
| WO2010065960A2 (fr) * | 2008-12-05 | 2010-06-10 | Semprus Biosciences Corp. | Compositions pour greffe de type « à partir de » anti-thrombogènes, antimicrobiennes et anti-encrassement |
-
2009
- 2009-09-22 FR FR0904509A patent/FR2950226B1/fr not_active Expired - Fee Related
-
2010
- 2010-07-26 JP JP2012530187A patent/JP2013505277A/ja active Pending
- 2010-07-26 EP EP10734753A patent/EP2480072A2/fr not_active Withdrawn
- 2010-07-26 US US13/497,212 patent/US20130005810A1/en not_active Abandoned
- 2010-07-26 CN CN2010800424969A patent/CN102711457A/zh active Pending
- 2010-07-26 WO PCT/EP2010/060792 patent/WO2011035949A2/fr not_active Ceased
- 2010-07-26 KR KR1020127010104A patent/KR20120101349A/ko not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2011035949A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011035949A3 (fr) | 2011-11-24 |
| US20130005810A1 (en) | 2013-01-03 |
| FR2950226B1 (fr) | 2012-04-06 |
| FR2950226A1 (fr) | 2011-03-25 |
| CN102711457A (zh) | 2012-10-03 |
| WO2011035949A2 (fr) | 2011-03-31 |
| JP2013505277A (ja) | 2013-02-14 |
| KR20120101349A (ko) | 2012-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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