US20120160254A1 - Cryotropic hydrogels and their use as filters - Google Patents

Cryotropic hydrogels and their use as filters Download PDF

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Publication number
US20120160254A1
US20120160254A1 US13/256,976 US201013256976A US2012160254A1 US 20120160254 A1 US20120160254 A1 US 20120160254A1 US 201013256976 A US201013256976 A US 201013256976A US 2012160254 A1 US2012160254 A1 US 2012160254A1
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Prior art keywords
filter
particle
smoke
hydrogel
cigarette
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US13/256,976
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English (en)
Inventor
Ashok Kumar
Haider Sami
Akshay Srivastava
Animangsu Ghatak
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Protista Biotechnology AB
Protista International AB
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Protista Biotechnology AB
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Assigned to PROTISTA INTERNATIONAL AB reassignment PROTISTA INTERNATIONAL AB ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KUMAR, ASHOK, SAMI, HAIDER, SRIVASTAVA, AKSHAY, GHATAK, ANIMANGSU
Publication of US20120160254A1 publication Critical patent/US20120160254A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/04—Tobacco smoke filters characterised by their shape or structure
    • A24D3/048—Tobacco smoke filters characterised by their shape or structure containing additives
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02—Manufacture of tobacco smoke filters
    • A24D3/0229—Filter rod forming processes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/062—Use of materials for tobacco smoke filters characterised by structural features
    • A24D3/066—Use of materials for tobacco smoke filters characterised by structural features in the form of foam or having cellular structure
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/067—Use of materials for tobacco smoke filters characterised by functional properties
    • A24D3/068—Biodegradable or disintegrable
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D39/00—Filtering material for liquid or gaseous fluids
    • B01D39/14—Other self-supporting filtering material ; Other filtering material
    • B01D39/16—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres
    • B01D39/1669—Cellular material
    • B01D39/1676—Cellular material of synthetic origin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
    • B01D2239/04—Additives and treatments of the filtering material
    • B01D2239/0414—Surface modifiers, e.g. comprising ion exchange groups
    • B01D2239/0421—Rendering the filter material hydrophilic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/20—Organic adsorbents
    • B01D2253/202—Polymeric adsorbents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/30—Physical properties of adsorbents
    • B01D2253/34—Specific shapes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
    • B01D2257/702—Hydrocarbons
    • B01D2257/7022—Aliphatic hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
    • B01D2257/702—Hydrocarbons
    • B01D2257/7027—Aromatic hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/93—Toxic compounds not provided for in groups B01D2257/00 - B01D2257/708

Definitions

  • the present invention relates to the field of cryotropic hydrogels and their use for filters.
  • the present invention further relates to the design of smoke filters including a cigarette smoke filter using crosslinked porous materials.
  • the invention further concerns a method for the filtration of smoke.
  • Cigarettes have always been a topic of conflict between the health organizations and the cigarette companies because of harmful and carcinogenic compounds.
  • filters have been designed using fibers made of thermoplastic polymeric materials.
  • U.S. Pat. No. 4,059,121 describes a filter element made of solid fibers oriented in randomly manner. The diameter of these fibers range up to 5 ⁇ m. While, this patent talks about a single filter element, U.S. Pat. No.
  • a bi-component sheath-core filter is envisaged by U.S. Pat. Nos. 5,633,082 and 6,026,819 which describe the use of thermoplastic material like polypropylene, polybutylene terephthalate and ethylene-vinyl acetate copolymer. These polymers in different composition are used to form the core and the sheath and a seamless continuity over these two regions. While the above patents desires essentially to achieve high filtration efficiency while maintaining the mechanical integrity of the filter, these are several other patents which have been proposed to improve the quality of smoke being inhaled, by the addition into the matrix of the filter of different components and molecules which either diffuse slowly into the smoke or arrest something toxic. For example, U.S. Pat. No.
  • 5,115,823 proposes to impart flavor to the smoke by a novel design which comprises of a filtering zone and a flavor enhancing zone containing the flavor.
  • U.S. Pat. Nos. 5,746,231 and 6,164,288 propose dispersing of a humectant like sodium pyroglutamate, chlorophyllin, vegetable oil etc. into the filtering material which captures the moisture in the smoke. This moisture then helps in wet filtering of the smoke.
  • U.S. Pat. No. 6,530,377 proposes to incorporate these molecules inside microcapsules dispersed through the matrix of the filter. Beside these humectants, there are other type of molecules that facilitate removal of toxic chemicals have been proposed. For example, U.S. Pat. No.
  • cryogel a polymeric material known as cryogel which have been found to reduce the particle count significantly (10 7 particles per centimeter cube) without increasing the pressure drop any significantly.
  • a particle-filter comprising at least one hydrogel formed in aqueous solution at a temperature below 0° C.
  • a cigarette comprising at least one particle-filter as described above.
  • “Cryogel” is used herein to denote a hydrogel formed in aqueous solution at subzero temperatures.
  • Hydrogel is used herein to denote a network of crosslinked water-soluble polymer chains.
  • a macroporous material is a material containing pores with an average diameter greater than 50 nm but not more than 50 ⁇ m, along with interconnectivity between the pores.
  • “Smoke” is used herein to denote a collection of airborne solid and liquid particulates and gases emitted when a material undergoes combustion or pyrolysis. For instance smoke often comprises particles comprising tar.
  • substances in cigarette smoke include but are not limited to methane, acetylene, ethane, propene, chloromethane, propane, ethanol, acetaldehyde, butene, ethanol, acetonitrile, acrolein, acetone, acrylonitrile, isoprene, pentadiene, 2-butanone, hexane, benzene, dimethylfuran, pyridine, toluene, benzopyrine, napthalene, N-nitrosamine, chloro-biphenyls, phenols, 2-pentanone, 3-buten-2-one, 3-pentanone, ethylbenzene, isobutyronitrile, isoprene, o-x
  • a supermacroporous material is a material comprising pores greater than 1000 nm (1 ⁇ m) along with interconnectivity between the pores.
  • FIG. 1 shows scanning electron microscope image of a typical cryogel sample.
  • the image shows the presence of pores and the pore wall made of the polymeric material.
  • the pore size is a function of the polymer and the crosslinker concentration.
  • FIG. 2 shows schematic of the experimental set up for particle count analysis in the smoke emitted by a burning cigarette.
  • the cigarette 21 is first attached to one end of a cylindrical holder 22 which contains also a smoke filter 23 .
  • This filter is either a conventional filter or one pre-designed of cryogel material.
  • the SMPS 25 (Scanning Mobility Particle Sizer Spectrophotometer) sucks in the smoke 24 at constant flow rate which brings in the tar and other content from the burning cigarette and analyze it to yield the particle size distribution of the smoke 24 .
  • FIG. 3 shows number density N p of particles per cc volume of smoke is plotted against diameter D p (nm) of particles.
  • N p of particles per cc volume of smoke is plotted against diameter D p (nm) of particles.
  • D particle count in smoke released respectively by a single (D) and double (C) conventional cigarette filter
  • E particle count in smoke released by John silver cigarette filter
  • FIG. 4 shows number density N p of particles per cc volume of smoke is plotted against diameter D p (nm) of particles.
  • N p of particles per cc volume of smoke is plotted against diameter D p (nm) of particles.
  • FIG. 5 shows number density N p of particles per cc volume in smoke released by the acrylamide cryogel filters prepared with varying monomer to cross-linker ratio plotted against the particle size D p in nm.
  • the monomer concentration is kept constant at 6%.
  • J denotes a 3:1 Cryogel
  • K denotes a 4:1 Cryogel.
  • FIG. 6 shows pressure drop (Pa) across the filters plotted against the flow rate (cc/min) of gas through the filters.
  • FIG. 7 shows Number density N p of particles per cc volume of smoke is plotted against diameter D p (nm) of particles. Comparison of particle reduction by agarose-alginate cryogel filters in wet (Q) and dry (P) condition.
  • a particle-filter comprising at least one hydrogel formed in aqueous solution at a temperature below 0° C.
  • a highly efficient particle-filter comprising a cross-linked inter-connected macroporous hydrogel structure to reduce particulate components in mainstream cigarette smoke.
  • a cigarette filter which has been prepared by using crosslinked material e.g. “cryogel” synthesized using acrylamide, or N-isopropylacrylamide monomers but not excluding others.
  • crosslinked material e.g. “cryogel” synthesized using acrylamide, or N-isopropylacrylamide monomers but not excluding others.
  • filters synthesized by cryogel matrices of synthetic polymers like agarose and/or alginate These materials are prepared without using any organic solvent and are biodegradable.
  • the filtration process is achieved via physical adsorption onto the surface of the cryogel material or by specific chemical reaction if the crosslinked network is suitably functionalized.
  • the filter is recyclable and biodegradable.
  • One advantage of the crosslinked structure is that it provides mechanical strength to the filter without significantly increasing the pressure drop. Furthermore, both these parameters can be tuned by controlling the pore size distribution.
  • This cigarette filter has been found to reduce the content of particles comprising tar in the cigarette smoke by several orders of magnitude from what is achieved by the conventional filters used in cigarettes.
  • the filter can be used in both wet and dry condition.
  • the macroporous nature and interconnectivity makes these cryogel filters as highly efficient substitutes of the conventional cigarette filters or can be used as an additional filter to the native cigarette filter.
  • the invention discloses the application of porous crosslinked materials like cryogel as the base material for designing cigarette smoke filters.
  • the cross linking polymerization is in one embodiment carried out inside a hollow solid cylinder in order to achieve a cylindrical structure (monolith) of the filter of specific dimensions to suit for application of use as filters.
  • the particle-filter is a cigarette filter.
  • the hydrogel of the particle-filter is insoluble in water.
  • the hydrogel of the particle-filter comprises water. This has the advantage that water arrests particles, for example particles comprising tar in cigarette smoke.
  • the hydrogel of the particle-filter is hydrophilic. This has the advantage that the filter contains water in its pores without allowing the water to wet the surface of its container, e.g. the paper wall of a conventional filter.
  • the hydrogel of the particle-filter is supermacroporous.
  • the hydrogel of the particle-filter comprises at least one material selected from the group consisting of poly-acrylamide, agarose, and alginate.
  • the hydrogel is formed at a temperature below ⁇ 10° C. In one embodiment the hydrogel is formed at a temperature below the freezing point of the solution comprising the monomer. In an alternative embodiment the hydrogel is formed at a temperature 10 degrees Celsius below the freezing point of the solution comprising the monomer.
  • the hydrogel of the particle filter is formed without using any organic solvents. This has the advantage that it does not cause harm to the environment and the human body.
  • a cigarette comprising at least one particle-filter as described above.
  • the at least one filter is recycled.
  • the at least one filter is washed with water, when it is recycled.
  • particulate matter in the smoke is reduced. In one embodiment the reduction of particulate matter is more than 95 wt %. In another embodiment the reduction of particulate matter is more than 99 wt %. In yet another embodiment the reduction of particulate matter is more than 99.9 wt %. In an alternative embodiment the reduction of particulate matter removes essentially all particles.
  • the amount of at least one substance in the smoke is reduced, wherein the at least one substance is at least one substance selected from the group consisting of methane, acetylene, ethane, propene, chloromethane, propane, ethanol, acetaldehyde, butene, ethanol, acetonitrile, acrolein, acetone, acrylonitrile, isoprene, pentadiene, 2-butanone, hexane, benzene, dimethylfuran, pyridine, toluene, benzopyrine, napthalene, N-nitrosamine, chloro-biphenyls, phenols, 2-pentanone, 3-buten-2-one, 3-pentanone, ethylbenzene, isobutyronitrile, isoprene, o-xylene, propionaldehyde, propionitrile, m-/p-xylene, styrene and tol
  • the amount of the above at least one substance in the smoke is reduced by more than 90 wt %. In a further embodiment the amount of the at least one substance in the smoke is reduced by more than 95 wt %. In another embodiment the amount of the at least one substance in the smoke is reduced by more than 99 wt %. In another embodiment the amount of the at least one substance in the smoke is reduced by more than 99.9 wt %.
  • the hydrogel is in an alternative embodiment made from at least one type of monomers or polymeric precursors selected from the group consisting of acrylamide, N-isopropylacrylamide, acrylonitrile, N-vinylcaprolactam, chitosan, gelatin, alginate, agarose and poly(vinylalcohol).
  • the cryogel is in one embodiment synthesized by using a polymerization reaction in the water medium under freezing conditions which yield a spongy, elastic and supermacroporous material. Normally the freezing conditions are below 0° C.
  • the filters according to the present invention are useful for filtering gases comprising particulate matter and substances in gas phase, for example the smoke generated by a cigarette, dust laden smoke in many industrial situations e.g. mines, blast furnaces, cement plants etc.
  • Cryogel filters can be employed in disposable particulate respirators for filtration of aerosols and fine particulates suspended in air, which are associated with human disorders like asthma, lung cancer etc.
  • cryogels of poly(acryl amide) [poly(AAm)] were synthesized by radical polymerization at ⁇ 12° C. during 12 hours using monomers of acryl amide (AAm) with N,N-ethylene bisacrylamide (MBAAm) as cross-linking agent.
  • MBAAm N,N-ethylene bisacrylamide
  • agarose-alginate cryogels were fabricated by cross-linking agarose and alginate with the help of glutaraldehyde at ⁇ 12° C. for 16 hours.
  • the water freezes and form nucleated crystals which grow and prevents the polymer reaction from occurring inside the crystals of water.
  • the gel is brought back to the normal temperature at which the crystals melt resulting in the porous structure.
  • the sizes of these pores depend on the polymer concentration, cross-linker concentration and the rate of cooling.
  • the moisture content of the filter is controlled by drying it to a desired extent.
  • hydrogels in hydrated state The supermacroporous nature of these hydrogels was defined visually by scanning electron microcopy and ESEM (hydrogels in hydrated state). The quantitative estimation was done by mercury porosimetry, uptake of water and cyclohexane. The evaluated pore size is up to 200 ⁇ m.
  • cryogels polymeric matrices called as “cryogels” to reduce the particulate count of smoke by using cryogels as auxiliary or substitute to conventional filters.
  • Cryogel filters have been used as auxiliary filters to observe reduction in total particle matter (TPM) in main stream cigarette smoke. Cigarette smoke coming out of the cigarette butt having a single conventional cigarette filter has about 10 9 particles per centimeter cube (“D” in FIG. 3 ). These “cryogel filters” are macroporous materials having many advantages over the currently used cigarette filters as they remove significantly higher number of particles comprising tar compared to traditional auxiliary filters like John Silver or Capstan's cigarette filter used as auxiliary filter. As can be seen in FIG. 3 , acrylamide cryogel (7% monomer, 2:1) as auxiliary filter reduces total particulate count by a factor of about 10 4 in comparison to TPM of cigarette having its filter (“D” in FIG. 3 ).
  • cryogel filters Even if an additional cigarette filter is used as auxiliary filter with the cigarette (“C”, FIG. 3 ) the TPM reduction is less in comparison to the reduction offered by cryogel filters. Similarly 6% acrylamide cryogel also reduces particulate count by a factor of 10 3 to 10 2 when compared to auxiliary Capstan cigarette filter and auxiliary John Silver filter respectively ( FIG. 3 ).
  • Agarose-alginate cryogel filter gives a particle reduction by a factor of 10 4 in comparison to the particle reduction by traditional cigarette filter, when both of them were used as auxiliary filters ( FIG. 4 ).
  • the synthesis protocol of the cryogel filters can be varied to design cigarette filters with desired reduction in particulate count and optimum draw resistance.
  • the particle count decreases e.g. the particle reduction offered by acrylamide cryogel filter with 7% (total monomer) concentration is higher than that offered by 6% acrylamide cryogel filter ( FIG. 3 ).
  • the particle count passing through “cryogel filter” also decreases ( FIG. 5 ). This change in porosity by varying the polymer concentration and the cross linker to polymer ratio gives the cryogel of different porosity which changes the total particulate count (TPM) in the smoke.
  • FIG. 6 shows that both acrylamide and agarose-alginate cryogel filters have comparable pressure drop as with capstan cigarette filter, thus making them eligible candidates for use as cigarette filters.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
US13/256,976 2009-03-16 2010-03-16 Cryotropic hydrogels and their use as filters Abandoned US20120160254A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE0950156-0 2009-03-16
SE0950156 2009-03-16
PCT/SE2010/050285 WO2010107375A1 (fr) 2009-03-16 2010-03-16 Hydrogels cryotropes et leur utilisation comme filtres

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PCT/SE2010/050285 A-371-Of-International WO2010107375A1 (fr) 2009-03-16 2010-03-16 Hydrogels cryotropes et leur utilisation comme filtres

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EP (1) EP2411113A4 (fr)
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CA (1) CA2758056A1 (fr)
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US20220022526A1 (en) * 2018-12-07 2022-01-27 Philip Morris Products S.A. Aerosol-generating article having biodegradable filtration material

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UA115782C2 (uk) 2012-03-28 2017-12-26 Філіп Морріс Продактс С.А. Рідкі тютюнові композиції
CN105661638B (zh) * 2016-01-26 2019-08-30 广东中烟工业有限责任公司 一种提高卷烟烟气中水分含量的方法
CN108948229B (zh) * 2018-06-29 2021-08-06 中南民族大学 一种4-甲基伞形酮富集材料及其用途
CN109619686A (zh) * 2018-12-28 2019-04-16 山东圣和塑胶发展有限公司 棒状多孔的电子烟气生成物的冷却元件及其制备方法
CN111067136A (zh) * 2019-11-13 2020-04-28 湖北中烟工业有限责任公司 一种用于低温卷烟降温段的材料及其制备方法及其应用

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KR20150010944A (ko) * 2012-04-30 2015-01-29 필립모리스 프로덕츠 에스.에이. 에어로졸을 포함하는 흡연 물품 마우스피스
KR102092622B1 (ko) 2012-04-30 2020-03-25 필립모리스 프로덕츠 에스.에이. 에어로젤을 포함하는 흡연 물품 마우스피스
US20220022526A1 (en) * 2018-12-07 2022-01-27 Philip Morris Products S.A. Aerosol-generating article having biodegradable filtration material

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EP2411113A1 (fr) 2012-02-01
WO2010107375A1 (fr) 2010-09-23
CA2758056A1 (fr) 2010-09-23
CN102740946A (zh) 2012-10-17
US20140113786A1 (en) 2014-04-24
EP2411113A4 (fr) 2014-10-29

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