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EP2137263A2 - Fabrication de pigment finement reparti - Google Patents

Fabrication de pigment finement reparti

Info

Publication number
EP2137263A2
EP2137263A2 EP08736041A EP08736041A EP2137263A2 EP 2137263 A2 EP2137263 A2 EP 2137263A2 EP 08736041 A EP08736041 A EP 08736041A EP 08736041 A EP08736041 A EP 08736041A EP 2137263 A2 EP2137263 A2 EP 2137263A2
Authority
EP
European Patent Office
Prior art keywords
pigment
acid
crystallization modifier
solid
aqueous diluent
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Withdrawn
Application number
EP08736041A
Other languages
German (de)
English (en)
Inventor
Joachim Jesse
Benno Sens
Richard Van Gelder
Matthias KLÜGLEIN
Wolfgang Best
Rainer Henning
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP08736041A priority Critical patent/EP2137263A2/fr
Publication of EP2137263A2 publication Critical patent/EP2137263A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/0086—Non common dispersing agents anionic dispersing agents

Definitions

  • the invention relates to a process for the formation of organic pigments using sulfonate-containing condensation products based on naphthalenesulfonic acid as crystallization modifiers.
  • Organic pigments often accumulate in the synthesis in coarsely crystalline form with very heterogeneous particle size distribution.
  • the crude pigments are therefore usually subjected to a formation for conversion into a coloristically valuable pigment form which is suitable for the application.
  • a grinding of the crude pigment and subsequent recrystallization of the millbase in an organic solvent is known, or the grinding is carried out as a wet grinding in aqueous suspension in high-speed stirred ball mills.
  • the methods described achieve particle size reduction and thus an improvement in the coloristic properties of the pigments, sometimes with a high expenditure of time, it is difficult to control the particle size of the pigments obtained, and the pigments are frequently used in a number of applications. For example, as a colorant in ink-jet inks, insufficient, because too broad particle size distribution on.
  • WO 02/00643 discloses a process for the formation of quinophthalone crude pigments, in which the crude pigment obtained in the synthesis is subjected to milling in the absence of milling aids and the resulting milled material is subsequently treated in the presence of a quinophthalone derivative in an organic solvent or a Crystallize mixture of organic solvent and water.
  • derivatives are sulfonic acid derivatives of quinophthalone pigments.
  • WO 2004/048482 discloses a process for the formation of organic pigments, in which the pigment is dissolved in concentrated sulfuric acid and the sulfuric acid solution is mixed with water in the presence of a condensation product of naphthalenesulfonic acid and formaldehyde as crystallization modifier.
  • the crystallization modifier is added before the mixing of the sulfuric acid pigment solution or it is in this by reaction of 1- and 2- Naphthalenesulfonic acid with formaldehyde generated in situ.
  • a disadvantage of this in-situ synthesis is that condensation products with broad and poorly defined molecular weight distribution result.
  • the object of the invention is to provide an advantageous and easy to carry out process for the formation of organic pigments, which gives pigments with very good coloristic properties.
  • the object is achieved by a method for forming (finishing) an organic see pigment, in which the pigment is dissolved or dispersed in a mineral acid and from the solution or dispersion, the pigment by mixing with an aqueous diluent in the presence of a sulfonate groups Condensation product of a naphthalenesulfonic acid and at least one aliphatic aldehyde having 1 to 6 carbon atoms crystallize as a crystallization modifier and then the pigment isolated as a solid, characterized in that the crystallization modifier is added with the aqueous diluent.
  • the particle size of the pigment particles can be better controlled.
  • the crystallization modifier is a condensation product of one or more naphthalenesulfonic acids, which may have one or more sulfonic acid groups, preferably 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid or mixtures thereof, and one or more different aliphatic aldehydes having 1 to 6 C-atoms. Preference is given to mixtures of 1-naphthalenesulfonic acid and 2-naphthalenesulfonic acid, for example in a molar ratio of 4: 1. In general, from 0.5 to 2 mol of aliphatic aldehyde are condensed per mole of naphthalenesulfonic acid present, and this molar ratio is particularly preferably about 1: 1.
  • Preferred aliphatic aldehyde is formaldehyde. Most preferably, only formaldehyde is used.
  • the naphthalenesulfonic acids are prepared by sulfonation of naphthalene with concentrated sulfuric acid or oleum. In this case, to a small extent, multiple sulfonated products and / or sulfones can be formed and consequently also be contained in the condensation products.
  • the crystallization modifier which is generally a commercial product and preferably present as a concentrated aqueous solution, simply becomes the aqueous one
  • the naphthalenesulfonic acid-aldehyde condensates used according to the invention as crystallization modifiers generally have an average molecular weight ⁇ 20,000 g / mol, preferably ⁇ 10,000 g / mol, more preferably from 500 to 15,000 g / mol and in particular from 1,000 to 10,000 g / mol.
  • the atomic ratio of sulfur to carbon is preferably at least 1: 11. Such condensation products are also commercially available.
  • naphthalenesulfonic acid-formaldehyde condensate can be prepared as follows:
  • 1 to 3 parts by weight of naphthalene are sulfonated with 1 to 3 parts by weight of a sulfuric acid having a concentration of 85 to 100 wt .-% or oleum having a free SO 3 content of 2 to 45 wt .-%.
  • the sulfonation can be carried out at temperatures of 80 to 190 0 C, the reaction times are from 0.5 to 10 hours.
  • the sulfonation aids such as boric acid may be present, preferably in a concentration of 0.5 to 5 wt .-%, based on sulfuric acid or oleum.
  • the reaction mixture is diluted with 0.5 to 2 parts of water and then with 0.3 to 1, 8 parts of aqueous formaldehyde solution having a concentration of 20 to 40 wt .-% of formaldehyde at a temperature of 80 to 180 0th C condenses.
  • the condensation mixture is then diluted with up to 0.5 parts of water and adjusted to a pH of 4 to 10 with sodium hydroxide solution.
  • the condensation mixture is finally diluted again with 0.5 part of water, treated with sodium hydroxide solution and lime milk and filtered off from precipitating CaSO 4 .
  • the pH is then adjusted to a value between 4 and 10.
  • the final concentration of 15 to 50% by weight of dry content is adjusted with water.
  • the condensation product generally acts as a crystallization inhibitor.
  • the organic pigment is dissolved or dispersed in a mineral acid and allowed to crystallize from the solution or dispersion by dilution with an aqueous diluent in the presence of the crystallization modifier.
  • Preferred mineral acid is sulfuric acid.
  • the pigment is dissolved in concentrated sulfuric acid.
  • the crystallization modifier is present when mixing the mineral acid pigment solution with the aqueous diluent in the aqueous diluent. In a preferred variant of this process, the mixing takes place by combining the mineral acid pigment solution and the crystallization modifier containing aqueous diluent by means of a mixing nozzle.
  • Aqueous diluent is generally water.
  • the crystallization can also be effected by pouring the mineral acid pigment solution into the aqueous diluent, preferably ice-water.
  • the crystallized organic pigment is allowed to mature in the presence of a surfactant.
  • the surfactant may already be added to the aqueous diluent or added after the crystallization step to the pigment suspension, generally as an aqueous solution.
  • the ripening of the crystallized organic pigment is generally carried out by stirring the pigment suspension at temperatures generally from 40 to 100 ° C. over a period of from 0.5 to 5 hours. This leads to the growth of larger pigment particles at the expense of smaller pigment particles and / or to a smoothing / healing of the crystal surface of the pigment particles.
  • Suitable surfactants are the anionic, cationic, nonionic and amphoteric surfactants mentioned below.
  • the concentration of the pigment in the mineral acid pigment solution is 5 to 30% by weight.
  • the crystallization modifier is generally used in amounts of from 0.1 to 30% by weight, based on the pigment.
  • the volume of the admixed aqueous diluent is generally 1 to 12 times the volume of the mineral acid pigment solution.
  • Suitable pigments which can be formed by the process according to the invention are, for example, azo, azomethine, methine, anthraquinone, phthalocyanine,
  • Preferred pigments are phthalocyanine, perylene,
  • Chinaeridone, indanthrone and quinophthalone pigments, dioxazine and diketopyrrolopyrrole, particularly preferred pigments are phthalocyanine, perylene and indanthrone pigments.
  • the crystallization modifier used according to the invention is generally present in amounts of from 0.1 to 30% by weight, preferably from 0.3 to 25% by weight, particularly preferably from 1 to 22% by weight, based on the pigment solution or Pigment suspension, before. In some cases it may be an advantage, besides others Use crystallization modifiers, dispersants, surfactants or special polymers. Examples of further crystallization modifiers are sulfonic acid-containing pigment derivatives or sulfonamides, such as imidazolemethyl- or pyrazolemethyl-quinone-pigmented sulfonic acids. These may be present during the precipitation step or added later.
  • surfactants examples include anionic surfactants such as alkylbenzenesulfonates or alkylnaphthalenesulfonates or alkylsulfosuccinates, cationic surfactants such as quaternary ammonium salts, for example benzyltributylammonium chloride, or nonionic or amphoteric surfactants such as polyoxyethylene surfactants and alkyl or amidopropyl betaines.
  • anionic surfactants such as alkylbenzenesulfonates or alkylnaphthalenesulfonates or alkylsulfosuccinates
  • cationic surfactants such as quaternary ammonium salts, for example benzyltributylammonium chloride
  • nonionic or amphoteric surfactants such as polyoxyethylene surfactants and alkyl or amidopropyl betaines.
  • the surfactants may be present during the precipitation step or added later.
  • Suitable special polymers are, for example, polyacrylic acid, polymethacrylic acid, polyurethanes, polyvinyl alcohol, polyvinylpyrrolidone or cellulose derivatives. These may be present during the precipitation step or added later.
  • the pigment obtained by precipitation and isolated as a solid is dispersed in dilute aqueous sulfuric acid and swollen in the presence of the crystallization modifier. It is advantageous to grind the pigment together with the crystallization modifier before swelling, for example in a stirred ball mill. Swelling leads to the growth of larger pigment particles at the expense of smaller pigment particles and / or to a smoothing / healing of the crystal surfaces of the pigment particles.
  • Suitable dilute sulfuric acid generally has a concentration of 50 to 85, preferably 60 to 85 wt .-% on.
  • the swelling of the pigment in the dilute aqueous sulfuric acid in the presence of the crystallization modifier is generally carried out at temperatures of 15 to 90 0 C over a period of generally 0.5 to 24 hours.
  • the optimum swelling conditions can be determined for each type of pigment in preliminary tests. Then it is diluted with water. To this end, 2 to 6 times as much water is added to the sulfuric acid pigment dispersion. Subsequently, stirring is generally continued for 0.5 to 2 hours.
  • the pigment obtained by precipitation and isolated as a solid is dispersed in water and crystallized in the presence of the crystallization modifier and an additive which increases the solubility of the pigment.
  • an organic solvent is added as the solubility enhancing additive. Suitable organic solvents are, for example, xylenes, glycols, alcohols, THF, acetone, NMP, DMF and nitrobenzene. These are added, based on the aqueous pigment suspension, generally in the amount of 0.1 to 50 wt .-%.
  • the amount of crystallization modifier is generally 0.1 to 30 wt .-%, based on the aqueous pigment suspension (without organic solvent).
  • the suspension is stirred in the presence of the organic solvent at temperatures in the range of 15 ° C. to the boiling point and then the organic solvent is distilled off.
  • the process can also be carried out without solvent under elevated pressure. In this case, a controlled by the crystallization modifier crystal growth of the pigment by Ostwald ripening takes place.
  • the pigment crystallized in the presence of the crystallization modifier is subsequently isolated as a solid by filtration of the aqueous suspension.
  • the pigment isolated as a solid is mixed with a pigment synergist.
  • a pigment synergist is generally a sulfonate-containing derivative of an organic pigment, generally a sulfonate-containing derivative of the aforementioned pigments.
  • the pigment synergist is the sulphonate group-containing derivative of the pigment with which the synergist is blended.
  • the pigment synergist is used in amounts of from 0.1 to 5% by weight, preferably from 1 to 10% by weight, based on the finished pigment formulation.
  • the average particle size of the formed pigments is generally in the range of 10 to 400 nm, preferably 20 to 200 nm.
  • the pigments formed by the process according to the invention may contain the crystallization modifier on the surface of the pigment particles.
  • the pigment preparations may contain further additives, generally in amounts of up to 15% by weight. Further additives are, for example, wetting agents, surfactants, antifoams, antioxidants, UV absorbers, stabilizers, plasticizers and texturizing aids.
  • the testing of the pigment preparations according to the invention takes place in an aqueous lacquer system.
  • a water tinting paste is first prepared based on a water-dilutable polyurethane resin.
  • this water tinting paste (15% strength by weight based on pigment) are added to 225 g of a polyurethane-based compounding varnish (described in Example 3 of WO-A 92/15405). After addition of 7.5 g of water, a pH of 8 is set with aminoethanol. The resulting suspension is stirred for 15 minutes with a propeller stirrer at 1000 rpm.
  • the pigment preparation is then made from the acid with a 25 0 C warm
  • a pigment preparation is obtained which, in an aqueous coating system based on a water-dilutable polyurethane resin, gives a strongly colored and transparent coating having a yellowish red hue.
  • the metallic finish is strong and brilliant.
  • this pigment preparation 50 parts of this pigment preparation are ground together with 3.75 parts of a sulfonic acid group-containing perylene compound (prepared according to Example 3 of EP 0 486 531 B1). With high transparency and yellowish red hue of Metalliclackie- tion, the aqueous coating system based on a water-dilutable polyurethane resin has a lower viscosity than that of the pigment preparation. 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

L'invention concerne un procédé de mise en forme (finition) d'un pigment organique, dans lequel le pigment est dissous ou dispersé dans un acide minéral et le pigment est amené à cristalliser à partir de la solution ou de la dispersion grâce au mélange avec un agent de dilution aqueux en présence d'un produit de condensation présentant des groupes sulfonate, issu d'un acide naphtaline sulfonique et d'au moins un aldéhyde aliphatique ayant 1 à 6 atomes de carbone en tant que modificateur de cristallisation et le pigment est ensuite isolé sous forme de matières solides, caractérisé en ce que le modificateur de cristallisation est présent dans l'agent de dilution aqueux.
EP08736041A 2007-04-13 2008-04-10 Fabrication de pigment finement reparti Withdrawn EP2137263A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08736041A EP2137263A2 (fr) 2007-04-13 2008-04-10 Fabrication de pigment finement reparti

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07106102 2007-04-13
EP08736041A EP2137263A2 (fr) 2007-04-13 2008-04-10 Fabrication de pigment finement reparti
PCT/EP2008/054319 WO2008125580A2 (fr) 2007-04-13 2008-04-10 Fabrication de pigment finement réparti

Publications (1)

Publication Number Publication Date
EP2137263A2 true EP2137263A2 (fr) 2009-12-30

Family

ID=39765217

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08736041A Withdrawn EP2137263A2 (fr) 2007-04-13 2008-04-10 Fabrication de pigment finement reparti

Country Status (6)

Country Link
US (1) US20100050904A1 (fr)
EP (1) EP2137263A2 (fr)
JP (1) JP2010523782A (fr)
KR (1) KR20100016422A (fr)
CN (1) CN101679765A (fr)
WO (1) WO2008125580A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009019180A2 (fr) * 2007-08-03 2009-02-12 Basf Se Procédé de formation de pigments organiques
CN102532938B (zh) * 2011-12-29 2013-07-03 苏州世名科技股份有限公司 含有超细酞菁颜料颗粒的颜料制备物的制备方法
US8808437B2 (en) * 2012-11-26 2014-08-19 Xerox Corporation Phase change inks containing quinacridone pigments and synergists
CN103773078A (zh) * 2014-01-24 2014-05-07 先尼科化工（上海）有限公司 纳米蒽醌类有机颜料的制造方法
CN115011138B (zh) * 2022-05-18 2023-11-17 宁夏彩妍科技有限公司 液晶显示屏用颜料红177的生产方法及生产系统

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Publication number Priority date Publication date Assignee Title
GB475882A (en) * 1935-06-01 1937-11-29 Ig Farbenindustrie Ag Process for the manufacture of highly dispersed pigments
US2334812A (en) * 1940-02-23 1943-11-23 Du Pont Process for the preparation of organic pigments
GB547411A (en) * 1940-02-23 1942-08-26 Du Pont Improvements in or relating to the manufacture of organic colouring materials
DE1183884B (de) * 1959-08-22 1964-12-23 Basf Ag Verfahren zur Herstellung eines Chinacridon-Pigments
DE1181160B (de) * 1961-07-29 1964-11-12 Bayer Ag Verfahren zur Herstellung feindisperser Farbstoffe oder Pigmente
GB1143727A (fr) * 1966-09-09 1900-01-01
US3713857A (en) * 1971-02-25 1973-01-30 Sun Chemical Corp Phthalocyanine pigments
US6648954B2 (en) * 2000-03-06 2003-11-18 Toyo Ink Mfg. Co., Ltd. Water-based pigment dispersion, use thereof and process for the production thereof
DE10049201A1 (de) * 2000-10-05 2002-04-11 Clariant Gmbh Verfahren zur Feinverteilung von organischen Pigmenten durch Fällung
US6902613B2 (en) * 2002-11-27 2005-06-07 Ciba Specialty Chemicals Corporation Preparation and use of nanosize pigment compositions
DE102005019400A1 (de) * 2005-04-25 2006-11-02 Basf Ag Grüne Pigmentzubereitungen auf Basis von C.I. Pigment Green 36
WO2007014915A1 (fr) * 2005-08-04 2007-02-08 Basf Se Dispersions aqueuses et leur utilisation
DE102005049327A1 (de) * 2005-10-12 2007-04-19 Basf Ag Verfahren zur Herstellung wässriger Emulsionen und Dispersionen
ATE546496T1 (de) * 2006-05-23 2012-03-15 Basf Se Verwendung von hyperverzweigten polycarbonaten als dispergiermittel für pigmente

Non-Patent Citations (1)

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Title
See references of WO2008125580A2 *

Also Published As

Publication number Publication date
KR20100016422A (ko) 2010-02-12
WO2008125580A2 (fr) 2008-10-23
CN101679765A (zh) 2010-03-24
JP2010523782A (ja) 2010-07-15
WO2008125580A3 (fr) 2009-04-09
US20100050904A1 (en) 2010-03-04

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