CN101463120B - Method for preparing polyurethane acid imide foam material - Google Patents
Method for preparing polyurethane acid imide foam material Download PDFInfo
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- CN101463120B CN101463120B CN2009100761815A CN200910076181A CN101463120B CN 101463120 B CN101463120 B CN 101463120B CN 2009100761815 A CN2009100761815 A CN 2009100761815A CN 200910076181 A CN200910076181 A CN 200910076181A CN 101463120 B CN101463120 B CN 101463120B
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Abstract
The invention discloses a method for preparing a polyurethaneimide foam material. A formula of the polyurethaneimide foam material consists of polyol, dianhydride, a foam stabilizer, a catalyst, an auxiliary agent, a foaming agent and polyisocyanate; a preparation process employs a PU or PI quasiprepolymerization method, and comprises the following steps: proportionally reacting part of the polyol with the polyisocyanate in the formula, proportionally reacting part of the dianhydride with all polyisocyanate in the formula to produce a PU or PI performed polymer with moderate viscosity and low molecular weight, then adding other components and the rest of the polyol or the dianhydride at high-speed stirring to make the polyurethaneimide foam material. The method has the advantages of simple preparation process, low energy consumption, wide adjustable foaming process range, increased process window width, easy control of a polymer structure and high production efficiency, and the prepared foam material product is characterized by evenly distributed rigid chain segments and flexible chain segments, improved orderliness of the polymer structure, excellent physical and mechanical properties and convenient popularization and application.
Description
Affiliated technical field
The present invention relates to polymeric material field, specifically relate to a kind of method for preparing polyurethane acid imide foam material.
Technical background
In polymeric material field, imide-urethane (Pulythane-imide, be called for short PUI) foam materials is that urethane (PU) and polyimide (PI) interpenetrate, cross development and a kind of new polymers foam materials of forming.The constructional feature of PUI is both to have contained the soft of urethane on its molecular chain, hard segment structure contains the imide structure of polyimide again, that is to say, the PUI material had both kept the soft of urethane, hard this agent structure of segment structure, but at its hard segment or/and comprise the polyimide segment in the soft chain segment, therefore the PUI material had both kept the premium properties of urethane substantially, the high flame retardant and the characteristic such as high temperature resistant of polyimide have been absorbed again, not only has the intensity height, from fire-retardant, high temperature resistant/low temperature, anti-solvent, resistance to oxidation, anti-irradiation, over-all propertieies such as dielectric properties are good, but also has light weight, thermal conductivity is low, adiabatic, sound absorption, characteristics such as gentle elasticity height, thereby not only can be used for aircraft, the naval vessel, military project high-tech areas such as armored vehicle also have purposes widely at civil areas such as building and boats and ships.
The preparation method of polyurethane acid imide foam material has single stage method and prepolymer method at present, the technical process of single stage method is that each component in the prescription is all once mixed, under high-speed stirring, make foam then, because mixing of materials, reaction, foaming are carried out simultaneously, therefore must use effective catalyst and suds-stabilizing agent, though single stage method is simple to operate, it is low to consume energy, but its polymer architecture is difficult to control, rigidity, soft segment skewness, microphase-separated is undesirable on the morphology, thereby physical and mechanical properties is relatively poor; The technical process of prepolymer method is that the manufacturing processed of foam materials was divided into for two steps, so claim two step method again, the first step is made the part performed polymer with the elder generation of the part component in foaming formulation hybrid reaction earlier, second step added other components respectively under high-speed stirring again, in chainpropagation, carry out foamable reaction, make foam at last, the advantage of prepolymer method is that the heat that polyreaction generates produced in the pre-polymerization stage, little heat in the foamable reaction process, can reduce the temperature of foam materials inner core greatly, avoid the foam block inner core sallow, the performed polymer viscosity is big, helps foam stabilization, its polymkeric substance rigidity, soft segment distributes more even, physical and mechanical properties is relatively good, shortcoming is that operation is many, complex operation, power consumption is high, and production efficiency is low, especially often because the viscosity of performed polymer itself is excessive, and make foamed forming process be difficult to carry out, can't obtain foam materials.Therefore, how to overcome the shortcoming that above-mentioned described preparation method exists, develop that a kind of preparation technology is simple, power consumption is low, polymer architecture is controlled easily, hard and soft property segment is evenly distributed, the method for preparing polyurethane acid imide foam material that physical and mechanical properties is good and production efficiency is high is the current problem of needing solution in the art badly.
Summary of the invention
The purpose of this invention is to provide that a kind of preparation technology is simple, power consumption is low, the foam process variable range wide, good process window width, production efficiency height are arranged, the hard and soft property of the foam materials of preparing segment is evenly distributed and the order height of polymer architecture, the method for preparing polyurethane acid imide foam material that the foam physics mechanical property improves.
In order to achieve the above object, the present invention is by the following technical solutions: a kind of method for preparing polyurethane acid imide foam material, by polyvalent alcohol, dianhydride, suds-stabilizing agent, catalyzer, auxiliary agent, whipping agent and polyisocyanates are formed the prescription of polyurethane acid imide foam material, be characterized in: preparation technology adopts quasi-prepolymer method, specifically be divided into urethane quasi-prepolymer method (PU quasi-prepolymer method) and two kinds of processing methodes of polyimide quasi-prepolymer method (PI quasi-prepolymer method), the PU quasi-prepolymer method is that part polyvalent alcohol in the prescription is reacted with whole polyisocyanates in proportion, generation has the moderate lower molecular weight PU performed polymer of viscosity, under high-speed stirring, other components and remaining polyvalent alcohol are added then, make foam materials; And the PI quasi-prepolymer method is that part dianhydride in the prescription is reacted with whole polyisocyanates in proportion, generates to have the moderate lower molecular weight PI performed polymer of viscosity, under high-speed stirring other components and remaining dianhydride is added then, makes foam materials;
Each constituent mass umber is in the polyurethane acid imide foam material prescription:
Polyvalent alcohol 20-90;
Dianhydride 10-80;
Suds-stabilizing agent: 0.1-3.5;
Catalyzer: 0.1-5.0;
Auxiliary agent: 5-60;
Whipping agent: 0.5-50;
Polyisocyanates: 20-200.
Above-mentioned described polyvalent alcohol raw material comprises: polyether glycol, polyester polyol, polyester ether polylol, radiation modification polyvalent alcohol, polymer polyatomic alcohol, polyolefin polyhydric alcohol, hydroxy-terminated polysiloxane, vegetable oil polyol, rosin ester polyvalent alcohol, ammonia ester polyol and polypropylene ester polyol.
Above-mentioned described dianhydride class raw material comprises pyromellitic acid dianhydride, 3,3,4,4-benzophenone tetracarboxylic dianhydride, butane tetracarboxylic dianhydride, tetramethylene tetracarboxylic dianhydride, pentamethylene tetracarboxylic dianhydride, hexanaphthene tetracarboxylic dianhydride and cyclooctadiene tetracarboxylic dianhydride.
Above-mentioned described polyisocyanates comprises polyphenyl polymethylene polyisocyanates (PAPI), tolylene diisocyanate (TDI), liquefaction diphenylmethanediisocyanate (liquefied mdi), isophorone diisocyanate (IPDI), dicyclohexyl methane diisocyanate (hydrogenation MDI), xylylene diisocyanate (XDI), hexamethylene diisocyanate (HDI), trimethylammonium-1,6-hexamethylene diisocyanate (TMDI), cyclohexanedimethyleterephthalate vulcabond (HXDI), norbornene alkyl diisocyanate (NBDI).
Above-mentioned described catalyzer is: the ethylene glycol solution (AE-33) of Tributylamine, 33% triethylenediamine, described stablizer is a silicone oil.
Above-mentioned described auxiliary agent comprises three (2-chloroethyl) phosphoric acid ester (TCEP).
Above-mentioned described whipping agent comprises chloro fluoroethane (HCFC-141b) and water.
The method for preparing polyurethane acid imide foam material adopts PU quasi-prepolymer method and PI quasi-prepolymer method, and wherein the processing step of PU quasi-prepolymer method is:
A. dianhydride class raw material is mixed with the liquefied compound auxiliary agent with solvent action, be prepared into pasty mixture;
B. 20%～80% polyvalent alcohol is mixed with polyisocyanates and make performed polymer, as first component;
C. will remain polyvalent alcohol and pasty mixture and suds-stabilizing agent, catalyzer, auxiliary agent, whipping agent and water and be mixed together, as second component;
D. first component and second component are mixed the back and inject mould and foam, thereby make the PUI foam materials;
And the processing step of PI quasi-prepolymer method is:
A. dianhydride class raw material is mixed with the liquefied compound auxiliary agent with solvent action, be prepared into pasty mixture;
B. 15%～90% mashed prod is mixed with polyisocyanates and make performed polymer, as first component;
C. will remain pasty mixture and polyvalent alcohol and suds-stabilizing agent, catalyzer, auxiliary agent, whipping agent is mixed together, as second component;
D. first component and second component are mixed the back and inject mould and foam, thereby make the PUI foam materials.
Cardinal principle of the present invention is, at first each component in the polyurethane acid imide foam material prescription is made two components in proportion respectively, i.e. first component and second component, then, after first component and second component mixed, inject mould immediately, foaming just obtains the foam materials product.Because the two viscosity of first component and second component is moderate, it is the greatest factor of control foaming process and foamy structure performance, quasi-prepolymer method of the present invention is compared with prepolymer method with single stage method of the prior art, can regulate material viscosity and frothy gel intensity better, help foam stabilization, and the order degree of polymer architecture is improved, thereby improve PUI foamy performance; Simultaneously, method of the present invention is regulated the viscosity of first component and second component with comparalive ease, this just can make mixing of materials even in a short period of time, demonstrate in the scope of broadness and regulate technology, these advantages with good process window width, and, because dianhydride class raw material is a solid, directly add, be difficult for mixing, in the present invention, used liquefied compound auxiliary agent that it is made into pasty mixture with solvent action, equal to have carried out pre-dispersed processing, help mixing of materials and get more even.
Owing to adopted the above-mentioned method for preparing polyurethane acid imide foam material, make that preparation technology of the present invention is simple, power consumption is low, the foam process variable range enlarges, the technology window width increases, polymer architecture is controlled easily, the production efficiency height, and the hard and soft property of the foam materials of preparing segment has been evenly distributed, has increased the order of polymer architecture, make the foam materials physical and mechanical properties strengthen, improved the foam materials over-all properties, be ideal polyurethane acid imide foam material product comparatively, reached the purpose of invention.
Description of drawings
Fig. 1 is the process flow diagram of PU quasi-prepolymer method in the inventive method
Fig. 2 is the process flow diagram of PI quasi-prepolymer method in the inventive method
Embodiment:
Below in conjunction with embodiment the present invention is described in further detail:
Embodiment 1
The PU quasi-prepolymer method prepares polyurethane acid imide foam material BYTF-11, and wherein the mass fraction of the prescription of polyurethane acid imide foam material BYTF-11 and each component thereof is:
Polyvalent alcohol: TEP-3033 35
Dianhydride: pyromellitic acid dianhydride (PMDA) 65
Suds-stabilizing agent: silicone oil 1.5
Catalyzer: Tributylamine 2
The ethylene glycol solution of 33% triethylenediamine (AE-33) 0.5
Auxiliary agent: three (2-chloroethyl) phosphoric acid ester (TCEP) 40
Whipping agent: water 1.5
Polyisocyanates: polymethylene multi-phenenyl isocyanate (PAPI) 70
By above-mentioned prescription, it is standby to take by weighing each component respectively, and Fig. 1 shows that its processing step is:
A. 65 parts of pyromellitic acid dianhydrides (PMDA) and 40 part of three (2-chloroethyl) phosphoric acid ester (TCEP) are mixed into pasty mixture;
B. 15 parts of polyvalent alcohol TEP-3033 are mixed with 70 parts of polyisocyanates and make performed polymer, as first component;
C. 20 parts of polyvalent alcohol TEP-3033 and pasty mixture, 1.5 parts of silicone oil, 2 parts of Tributylamines, 0.5 part of AE-33 and 1.5 parts of water are mixed together, as second component;
D. first component and second component are mixed the back and inject mould and foam, depanning after the slaking obtains polyurethane acid imide foam material.
The performance of the sample BYTF-11 polyurethane acid imide foam material that present embodiment makes is as follows,
Density (g/cm
3) 0.039
Oxygen index (%) 32
Thermostability (TG method mensuration):
5% thermal weight loss temperature in the air (℃) 180.84
20% residual grey amount temperature in the air (℃) 252.04
Thermal conductivity (w/ (mk)) 0.0399
Standing-wave-tube method average sound absorption coefficient (125-4000Hz, 30mm) 0.31.
Embodiment 2
The PU quasi-prepolymer method prepares polyurethane acid imide foam material BYTF-8, and wherein the mass fraction of the prescription of polyurethane acid imide foam material BYTF-8 and each component thereof is:
Polyvalent alcohol: TEP-3033 10
H8305 20
Dianhydride: pyromellitic acid dianhydride (PMDA) 70
Suds-stabilizing agent; : silicone oil 1.5
Catalyzer: Tributylamine 2
The ethylene glycol solution of 33% triethylenediamine (AE-33) 0.5
Auxiliary agent: three (2-chloroethyl) phosphoric acid ester (TCEP) 40
Whipping agent: chloro fluoroethane (HCFC-141b) 30
Water 0.5
Polyisocyanates: polymethylene multi-phenenyl isocyanate (PAPI) 70
Processing step just changes step into 20 parts of polyvalent alcohol H8305 with 15 parts of polyvalent alcohol TEP-3033 among the b with embodiment 1; 20 parts of polyvalent alcohol TEP-3033 among the c are changed step into 10 parts.
The performance of the sample BYTF-8 polyurethane acid imide foam material that present embodiment makes is as follows,
Density (g/cm
3) 0.028
Oxygen index (%) 33
Thermostability (TG method mensuration):
5% thermal weight loss temperature in the air (℃) 179.40
20% residual grey amount temperature in the air (℃) 223.13
Thermal conductivity (w/ (mk)) 0.0394
Standing-wave-tube method average sound absorption coefficient (125-4000Hz, 30mm) 0.027.
Embodiment 3
The PU quasi-prepolymer method prepares polyurethane acid imide foam material BYTF-6, and wherein the mass fraction of the prescription of polyurethane acid imide foam material BYTF-6 and each component thereof is:
Polyvalent alcohol: H8305 30
PS-1752 10
Dianhydride: pyromellitic acid dianhydride (PMDA) 60
Catalyzer: Tributylamine 2
The ethylene glycol solution of 33% triethylenediamine (AE-33) 0.5
Suds-stabilizing agent: silicone oil 1.5
Auxiliary agent: three (2-chloroethyl) phosphoric acid ester (TCEP) 40
Whipping agent: chloro fluoroethane (HCFC-141b) 35
Water 0.5
Polyisocyanates: polymethylene multi-phenenyl isocyanate (PAPI) 75
Processing step just makes step into 20 parts of polyvalent alcohol H8305 with 15 parts of polyvalent alcohol TEP-3033 among the b with embodiment 1; 20 parts of polyvalent alcohol TEP-3033 among the c are changed step into 10 parts of polyvalent alcohol H8305 and 10 parts of polyvalent alcohol PS-1752.
The performance of the sample BYTF-6 polyurethane acid imide foam material that present embodiment makes is as follows,
Density (g/cm
3) 0.031
Oxygen index (%) 30
Thermostability (TG method mensuration):
5% thermal weight loss temperature in the air (℃) 183.63
20% residual grey amount temperature in the air (℃) 230.54
Thermal conductivity (w/ (mk)) 0.0406
Standing-wave-tube method average sound absorption coefficient (125-4000Hz, 30mm) 0.20.
Embodiment 4
The PU quasi-prepolymer method prepares polyurethane acid imide foam material BYTF-7, and wherein the mass fraction of the prescription of polyurethane acid imide foam material BYTF-7 and each component thereof is:
Polyvalent alcohol: H8305 25
BY-3080 10
Dianhydride: pyromellitic acid dianhydride (PMDA) 65
Suds-stabilizing agent: silicone oil 1.5
Catalyzer: Tributylamine 2
The ethylene glycol solution of 33% triethylenediamine (AE-33) 0.5
Auxiliary agent: three (2-chloroethyl) phosphoric acid ester (TCEP) 40
Whipping agent: chloro fluoroethane (HCFC-141b) 35
Water 1.5
Polyisocyanates: polymethylene multi-phenenyl isocyanate (PAPI) 70
Processing step just makes step into 25 parts of polyvalent alcohol H8305 with 15 parts of polyvalent alcohol TEP 3033 among the b with embodiment 1; 20 parts of polyvalent alcohol TEP-3033 among the c are changed step into 10 parts of polyvalent alcohol BY-3080.
The performance of the sample BYTF-7 polyurethane acid imide foam material that present embodiment makes is as follows,
Density (g/cm
3) 0.025
Oxygen index (%) 31
Thermostability (TG method mensuration):
5% thermal weight loss temperature in the air (℃) 184.15
20% residual grey amount temperature in the air (℃) 226.89
Thermal conductivity (w/ (mk)) 0.0389
Standing-wave-tube method average sound absorption coefficient (125-4000Hz, 30mm) 0.21.
Embodiment 5
The PI quasi-prepolymer method prepares polyurethane acid imide foam material BYTF-9, and wherein the mass fraction of the prescription of polyurethane acid imide foam material BYTF-9 and each component thereof is:
Polyvalent alcohol: H8305 20
TEP-3033 10
Dianhydride: pyromellitic acid dianhydride (PMDA) 70
Suds-stabilizing agent: silicone oil 1.5
Catalyzer: Tributylamine 2
The ethylene glycol solution of 33% triethylenediamine (AE-33) 0.5
Auxiliary agent: three (2-chloroethyl) phosphoric acid ester (TCEP) 40
Whipping agent: chloro fluoroethane (HCFC-141b) 30
Water 0.5
Polyisocyanates: polymethylene multi-phenenyl isocyanate (PAPI) 70
By above-mentioned prescription, it is standby to take by weighing each component respectively, and Fig. 2 shows that its processing step is:
The processing step of PI quasi-prepolymer method is:
A. 70 parts of dianhydride class raw material pyromellitic acid dianhydrides are mixed with 40 part of three (2-chloroethyl) phosphoric acid ester (TCEP) auxiliary agent, be prepared into pasty mixture
B. 30 parts of pasty mixtures are mixed with 70 parts of polyisocyanates and make performed polymer, as first component;
C. will remain 80 parts of pasty mixtures and 30 parts of polyvalent alcohols and 1.5 parts of silicone oil, 2 parts of Tributylamines, 30 parts of chloro fluoroethanes (HCFC-141b) and 0.5 part of water are mixed together, as second component;
D. first component and second component are mixed the back and inject mould and foam, obtain polyurethane acid imide foam material thereby make.
The performance of the sample BYTF-9 polyurethane acid imide foam material that present embodiment makes is as follows,
Density (g/cm
3) 0.023
Oxygen index (%) 32
Thermostability (TG method mensuration):
5% thermal weight loss temperature in the air (℃) 179.00
20% residual grey amount temperature in the air (℃) 224.50
Thermal conductivity (w/ (mk)) 0.0387
Standing-wave-tube method average sound absorption coefficient (125-4000Hz, 30mm) 0.24.
Embodiment 6
The PI quasi-prepolymer method prepares polyurethane acid imide foam material BYTF-10, and wherein the prescription of polyurethane acid imide foam material BYTF-10 and each constituent mass umber thereof are:
Polyvalent alcohol: TEP-3033 35
Dianhydride: pyromellitic acid dianhydride (PMDA) 65
Catalyzer: Tributylamine 2
The ethylene glycol solution of 33% triethylenediamine (AE-33) 0.5
Suds-stabilizing agent: silicone oil 1.5
Auxiliary agent: three (2-chloroethyl) phosphoric acid ester (TCEP) 40
Whipping agent: water 1.5
Polyisocyanates: polymethylene multi-phenenyl isocyanate (PAPI) 70.
Processing step just makes step into 50 parts of pasty mixtures with 30 parts among the b with embodiment 5; 80 parts of pasty mixtures among the c are made step into 55 parts of pasty mixtures.
The performance of the sample BYTF-10 polyurethane acid imide foam material that present embodiment makes is as follows,
Density (g/cm
3) 0.027
Oxygen index (%) 33
Thermostability (TG method mensuration):
5% thermal weight loss temperature in the air (℃) 177.79
20% residual grey amount temperature in the air (℃) 235.02
Thermal conductivity (w/ (mk)) 0.0410
Standing-wave-tube method average sound absorption coefficient (125-4000Hz, 30mm) 0.30.
Claims (7)
1. method for preparing polyurethane acid imide foam material, by polyvalent alcohol, dianhydride, suds-stabilizing agent, catalyzer, auxiliary agent, whipping agent and polyisocyanates are formed the prescription of polyurethane acid imide foam material, it is characterized in that: preparation technology adopts quasi-prepolymer method, specifically be divided into two kinds of processing methodes of PU quasi-prepolymer method and PI quasi-prepolymer method, the PU quasi-prepolymer method is that part polyvalent alcohol in the prescription is reacted with whole polyisocyanates in proportion, generation has the moderate lower molecular weight PU performed polymer of viscosity, under high-speed stirring, other components and remaining polyvalent alcohol are added then, make foam materials; And the PI quasi-prepolymer method is that part dianhydride in the prescription is reacted with whole polyisocyanates in proportion, generates to have the moderate lower molecular weight PI performed polymer of viscosity, under high-speed stirring other components and remaining dianhydride is added then, makes foam materials;
Each constituent mass umber is in the polyurethane acid imide foam material prescription:
Polyvalent alcohol: 20-90;
Dianhydride: 10-80;
Suds-stabilizing agent: 0.1-3.5;
Catalyzer: 0.1-5.0;
Auxiliary agent: 5-60;
Whipping agent: 0.5-50;
Polyisocyanates: 20-200;
Wherein, described auxiliary agent is three (2-chloroethyl) phosphoric acid ester.
2. according to the described method for preparing polyurethane acid imide foam material of claim 1, it is characterized in that: described polyvalent alcohol raw material comprises polyether glycol, polyester polyol, polyester ether polylol, radiation modification polyvalent alcohol, polyolefin polyhydric alcohol, hydroxy-terminated polysiloxane, vegetable oil polyol and rosin ester polyvalent alcohol.
3. according to the described method for preparing polyurethane acid imide foam material of claim 1, it is characterized in that: described dianhydride class raw material comprises pyromellitic acid dianhydride, 3,3,4,4-benzophenone tetracarboxylic dianhydride, butane tetracarboxylic dianhydride, tetramethylene tetracarboxylic dianhydride, pentamethylene tetracarboxylic dianhydride and hexanaphthene tetracarboxylic dianhydride.
4. according to the described method for preparing polyurethane acid imide foam material of claim 1, it is characterized in that: described polyisocyanates is selected from polyphenyl polymethylene polyisocyanates, tolylene diisocyanate, liquefaction diphenylmethanediisocyanate, isophorone diisocyanate, dicyclohexyl methane diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, trimethylammonium-1,6-hexamethylene diisocyanate, cyclohexanedimethyleterephthalate vulcabond or norbornene alkyl diisocyanate.
5. according to the described method for preparing polyurethane acid imide foam material of claim 1, it is characterized in that: described catalyzer is the ethylene glycol solution of Tributylamine and 33% triethylenediamine, and described stablizer is a silicone oil.
6. according to the described method for preparing polyurethane acid imide foam material of claim 1, it is characterized in that: above-mentioned described whipping agent comprises chloro fluoroethane (HCFC-141b) and water.
7. according to the described method for preparing polyurethane acid imide foam material of claim 1, it is characterized in that: described preparation method adopts PU quasi-prepolymer method and PI quasi-prepolymer method, and wherein the processing step of PU quasi-prepolymer method is:
A. dianhydride class raw material is mixed with the liquefied compound auxiliary agent with solvent action, be prepared into pasty mixture;
B. 20%～80% polyvalent alcohol is mixed with polyisocyanates and make performed polymer, as first component;
C. will remain polyvalent alcohol and pasty mixture and suds-stabilizing agent, catalyzer, auxiliary agent, whipping agent is mixed together, as second component;
D. first component and second component are mixed the back and inject mould and foam, thereby make the PUI foam materials;
And the processing step of PI quasi-prepolymer method is:
A. dianhydride class raw material is mixed with the liquefied compound auxiliary agent with solvent action, be prepared into pasty mixture;
B. 15%～90% pasty mixture is mixed with polyisocyanates and make performed polymer, as first component;
C. will remain pasty mixture and polyvalent alcohol and suds-stabilizing agent, catalyzer, auxiliary agent, whipping agent is mixed together, as second component;
D. first component and second component are mixed the back and inject mould and foam, thereby make the PUI foam materials.
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| CN101463120A (en) | 2009-06-24 |
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