KR20140070682A - Esterquat and preparation method thereof - Google Patents
Esterquat and preparation method thereof Download PDFInfo
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- KR20140070682A KR20140070682A KR20120124094A KR20120124094A KR20140070682A KR 20140070682 A KR20140070682 A KR 20140070682A KR 20120124094 A KR20120124094 A KR 20120124094A KR 20120124094 A KR20120124094 A KR 20120124094A KR 20140070682 A KR20140070682 A KR 20140070682A
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- South Korea
- Prior art keywords
- ester
- exchange reaction
- fabric softener
- ester exchange
- reaction
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
The present invention relates to an ester quat and a method for producing the same, and more particularly, to an ester quat and a method for producing the ester quart (EQ) Or a mixture thereof, thereby increasing the long-term stability and usability of the fabric softener, and a fabric softening agent containing the same.
The fabric softening agent is a finishing agent for imparting flexibility to fibers after washing, and usually provides an effect of imparting flexibility to fibers as well as an antistatic effect.
Generally, a textile softener is a dimethyl dialkyl ammonium chloride (DDAC) series or an ester quart (EQ) series. DDAC series fabric softener has high viscosity and high stability of product, but it is expensive and environmentally problematic. On the other hand, EQ series fabric softeners are low in viscosity and low in stability, but are inexpensive and environmentally friendly compared to DDAC.
EQ series fabric softeners are usually prepared by mixing water with additives such as EQ and fragrance. Recently, however, there has been a great demand for a fabric softener of EQ series having a viscosity of 300-600 cps which is significantly improved in viscosity than 15-50 cps, which is the viscosity of conventional fabric softener, have.
In response to this demand, attempts have been made to increase the viscosity of the final fabric softener using a thickener when mixing EQ with water. However, since the thickener is vulnerable to water, the process of securing the viscosity when mixing the thickener with water is very complicated and difficult. In addition, since the non-converted glyceride and glyceryl ester contained in the EQ increase the excessive price of the final fabric softener And a problem that stability is lowered.
In order to solve the problems of the prior art as described above, the present invention has been made to improve the feeling of use, productivity and long-term stability of the fabric softener without decreasing the content of glycerin and glyceride, And an ester quat, a fabric softening agent and a method for producing the same which can enhance the stability.
In the present invention, a primary ester exchange reaction is carried out at a temperature of 110-130 ° C. under a pressure of 50 mmHg or less such that a reaction molar ratio of an oil containing a fatty acid and a hydroxyalkylamine is 2: 1 to 3: 1 , And when 40-60% of the oil is converted into the reactant Followed by a second ester exchange reaction at a temperature of 130-160 < 0 > C to prepare a fatty acid hydroxyalkylamine ester; And reacting the produced fatty acid hydroxyalkylamine ester with a quaternizing agent in a solvent to prepare a fabric softener comprising an ester quat of the following formula 1:
In Formula 1,
A and B are each independently CH 2 CH 2 OH or CH 2 CH 2 OCR 2 ,
R 1 and R 2 are each independently selected from the group consisting of C 11 -C 21 linear or branched alkyl, alkenyl, and combinations thereof.
The present invention also provides an ester quat prepared by the above method.
The present invention also provides a process for preparing a fabric softener comprising the step of mixing the ester quart with water.
The present invention also provides a fabric softener comprising the ester quart.
The ester quat and the fabric softening agent according to the present invention can remarkably improve the viscosity as compared with the conventional EQ series fabric softener without use of the thickener, thereby enhancing the feeling of use, productivity and long-term stability of the fabric softener.
The present inventors have filed a Korean Patent Application No. 10-2011-25325, and have found that the ester exchange reaction for producing ester quats reduces the residues of glycerin, glyceride or a mixture thereof by a low-temperature high-vacuum reaction, In addition to excellent color improvement effect and long-term storage stability without injecting decolorant, it has been patented with patent registration No. 1050726 to improve the flexibility of fiber.
However, even in the case of ester quat according to the above method, in order to improve the high viscosity, feeling of use and long-term stability of the fabric softener required by the consumer, it is still necessary to use a thickener when mixing the ester quat with water, It has been difficult to completely solve the problem of high cost and deterioration of product stability due to complicated viscosity improvement process in order to manufacture a fabric softener having high viscosity because the thickener is vulnerable to water.
Accordingly, the inventors of the present invention have found that when ester quat is prepared by changing the reaction molar ratio of the fatty acid-containing oil and the tertiary hydroxyalkylamine to 1.7: 1, which is conventionally recognized in the production of ester quat, When the fabric softener is prepared by mixing water with quarts, it is confirmed that the viscosity of the final fabric softener is increased with the increase of the reaction molar ratio of the oil. Thus, without the use of the weaker accelerator, the fiber of 30-600 cps It was confirmed that the preparation of a softener was possible, and the present invention was completed.
Hereinafter, the present invention will be described in detail. In the present invention, the contents of the Korean Patent Application No. 10-2011-25325 are applied mutatis mutandis.
The process for producing ester quat according to the present invention is characterized in that the reaction molar ratio of the fatty acid-containing oil and the hydroxyalkylamine is 2: 1 - 3: 1 under a pressure of 50 mmHg or lower, Ester exchange reaction, and when 40-60% of the oil has been converted to the reactant Followed by a second ester exchange reaction at a temperature of 130-160 < 0 > C to prepare a fatty acid hydroxyalkylamine ester; And reacting the produced fatty acid hydroxyalkylamine ester with a quaternizing agent in a solvent.
In one embodiment of the present invention, the ester exchange reaction and the quaternization reaction can be performed in a closed reactor in which a vacuum pump and a glycerin storage tank are connected. For example, an enclosed reactor is connected to a glycerine reservoir through a pipe, a glycerin reservoir is connected to a vacuum pump, under certain conditions, the gaseous glycerin in the reactor is vented through the connected pipe to the reactor, It is changed into a liquid phase while passing through to the connected glycerin reservoir. Under certain temperature and pressure conditions, glycerin is vaporized and discharged through a pipe connected to the reactor under low pressure. Considering the reactor temperature and pressure, it is preferable that glycerin is discharged out of the reactor under the second reaction condition during the ester exchange reaction. After the ester exchange reaction, glycerin and glyceride contents in the reactants are very low. Thus, the content of glycerin and glyceride in the final fabric softener is lowered to obtain a superior fabric softener. In addition, the recovered glycerin can be used as a solvent in the quaternization reaction.
The process will be described in detail below.
In the present invention, the ester exchange reaction is a step of producing a fatty acid hydroxyalkylamine ester by an ester exchange reaction between an oil and a tertiary hydroxyalkylamine. In the present invention, the reaction molar ratio of the fatty acid-containing oil and the hydroxyalkylamine is 2: 1 - 3: 1. If the content of the oil in the reaction molar ratio is less than 2, the viscosity of the final fabric softener may be lower than 300 cps, which may make it difficult to achieve desired usability and stability. If the oil content is more than 3, There is a risk of scumming in the production of a softener.
Specifically, an oil containing a fatty acid and a tertiary hydroxyalkylamine are firstly subjected to a primary ester exchange reaction at a temperature of 110-130 ° C under a pressure of 50 mmHg or lower, and the temperature is elevated to perform a secondary ester exchange reaction at 130-160 ° C To produce a fatty acid hydroxyalkylamine ester.
Preferably, the higher the amount of the fatty acid contained in the oil, the more the flexibility of the fiber can be improved in the production of the ester quaternity. Therefore, triglycerides containing a large amount of substituents in the form of fatty acid, for example, palm oil containing a fatty acid, Vegetable oils such as olive oil, coconut oil, olive oil, soybean oil and cottonseed oil, or animal oils such as tallow, lard, and fish oil.
Examples of the tertiary hydroxyalkylamine that can be used in the present invention include diethanol methylamine, 1,2-dihydroxypropyl dimethylamine, triethanolamine, etc. Among them, Can be mixed and used.
Examples of the catalysts usable in the present invention include sodium alkoxide-based catalysts such as sodium methoxide, sodium ethoxide, sodium propoxide or sodium butoxide; A titanium oxide-based catalyst such as titanium oxide; Zinc oxide-based catalysts such as zinc oxide; Alkali catalysts such as silica, sodium hydroxide, potassium hydroxide, calcium hydroxide and anhydrous sodium carbonate; Or sodium hypophosphite. These may be used singly or in combination of two or more.
Among these, it is environmentally friendly, nontoxic to the human body, and excellent in reactivity, so that hydrolysis can be rapidly performed by only a small amount of water in the air or solvent, and a highly active photocatalyst such as titanium oxide is formed by heating and drying at a relatively low temperature , A titanium oxide-based catalyst or a zinc oxide-based catalyst is preferably used in that a function of a photocatalyst such as an antibacterial function and a malodor can be added to a fabric softener using the same. More preferably, the catalyst may comprise at least one selected from the group consisting of a sodium alkoxide-based catalyst, a titanium oxide-based catalyst, a zinc oxide-based catalyst, a silica, and an alkali catalyst, and a sodium hypophosphite additive .
The catalyst is preferably used in an amount of 0.03 to 0.1 part by weight based on 100 parts by weight of the total of the fatty acid-containing oil and the tertiary hydroxyalkylamine.
More preferably, the alkali catalyst and sodium hypophosphite are used in an amount of 0.03 to 0.1 part by weight based on 100 parts by weight of the total of the oil containing the fatty acid and the tertiary hydroxyalkylamine, respectively, .
In the ester exchange reaction, the primary ester exchange reaction is carried out at a temperature range of 110 to 130 ° C for 3 to 10 hours, and the secondary ester exchange reaction may be carried out at a temperature of 130 to 160 ° C for 1 to 13 hours. More specifically, when the ester exchange reaction is carried out without a catalyst, the first ester exchange reaction is preferably carried out for 6-10 hours and the second ester exchange reaction is preferably carried out for 5-13 hours. When the catalyst is used, The primary exchange reaction can be carried out for 3 to 7 hours and the secondary ester exchange reaction for 5 to 13 hours.
The pressure condition for the ester exchange reaction is 0-50 mmHg, and preferably the pressure of the second ester exchange reaction is lower than the pressure of the first ester exchange reaction. If the reaction pressure of the second ester exchange reaction is lower than that of the first ester exchange reaction, the glycerin can be recovered more advantageously. Preferably, the pressure of the primary ester exchange reaction of the present invention is 10-50 mmHg, more preferably 10-20 mmHg, and the pressure of the secondary ester exchange reaction is 0-10 mmHg, more preferably 0-5 mmHg. When the temperature and the vacuum pressure are out of the above-mentioned range, there is a possibility that a large amount of untranslated triglyceride oil is contained, which causes poor color and long-term stability.
In the first ester exchange reaction, when the reaction temperature is increased to call the second ester exchange reaction, the conversion can be performed when 40-60% of the oil is converted into the reactant. By weight. For example, if 60% of the oil is converted to reactant, the glycerin content may be 5-7 parts by weight relative to 100 parts by weight of the initial oil. The end point of the second ester exchange reaction may also be performed at a point of time when the oil is converted to a reaction product of 98% or more of oil, and the conversion of the oil may be measured by measuring the content of glycerin produced. In the above reaction, unreacted triglyceride material is increased when the oil is reacted at less than 40% in the primary ester exchange reaction, and the color of the product is lowered when the oil is reacted at 60% or more.
In the present invention, the quaternization reaction is a step of reacting the fatty acid hydroxyalkylamine ester obtained in the above ester exchange reaction with a quaternizing agent in a solvent to prepare an ester quat.
Examples of the organic solvent usable in the present invention include lower alcohols having 1 to 6 carbon atoms such as ethyl alcohol, propyl alcohol and isopropyl alcohol; Alkylene glycols having 1 to 6 carbon atoms such as ethylene glycol, diethylene glycol, propylene glycol, and polyethylene glycol; Glycerin, etc. These may be used singly or in combination of two or more. Preferably, a lower alcohol having 1 to 6 carbon atoms is preferable, and isopropyl alcohol is most preferable.
The solvent is preferably used in an amount of 5-30 parts by weight based on 100 parts by weight of the fatty acid hydroxyalkylamine ester.
Quaternizing agents which can be used in the present invention include alkyl halides such as methyl chloride; Dialkyl phosphates such as dimethyl sulfate and the like; Dialkyl carbonate such as dimethyl carbonate, diethyl carbonate and the like may be used. Of these, one type may be used alone or two or more types may be used in combination.
The fatty acid hydroxyalkylamine ester and the quaternizing agent are preferably contained in a reaction molar ratio of 1: 0.9-1: 1. If the reaction molar ratio is less than 1: 0.9, the unreacted alkylamine ester may increase and the emulsifying property may be lowered. If the molar ratio is more than 1: 1, unreacted quaternizing agent may remain in the product, May occur.
The quaternization reaction is preferably carried out at 35-50 ° C for 3-10 hours, preferably at 45-50 ° C for 3-6 hours.
The ester quat is prepared by the above-mentioned preparation method, and the ester quat can be represented by the following formula 1, for example.
[Chemical Formula 1]
In Formula 1,
A and B are each independently CH 2 CH 2 OH or CH 2 CH 2 OCR 2 ,
R 1 and R 2 are each independently selected from the group consisting of C 11 -C 21 linear or branched alkyl, alkenyl, and combinations thereof.
The present invention also provides a fabric softener comprising a fabric softener comprising an ester quat prepared by the above process and a step of mixing the ester quart with water.
In the present invention, the fabric softening agent is preferably 1-20 wt% of the ester quartz; And residual water. In addition, the fabric softener of the present invention may further contain 0.001 to 5 wt% of various additives such as fragrance, antifoaming agent, dye, preservative, etc. which can be mixed in the production of a conventional fabric softener.
The fabric softener according to the present invention can be manufactured at a desired viscosity of 300 to 600 cps without mixing a thickener when mixing the ester quat with water. The fabric softener according to the present invention is superior in usability and product stability Can be significantly improved.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
≪ Example 1 >
(1) ester exchange reaction
The reactor used in the present reaction was prepared by mixing 450 g of palmsteen oil and 110 g of triethanolamine in a four-necked sealed glass reactor equipped with a stirrer, a vacuum pump, a thermometer, a condenser, a recovered glycerin reservoir and a distillation device. The speed of the stirrer was fixed at 300-400 rpm and the temperature of the reaction mixture was raised to 125 캜 under a pressure of 10 mmHg by operating a vacuum device and the primary ester exchange reaction was carried out at this temperature for 7 hours.
The glycerin content in the reactor was continuously measured at intervals of 1 hour. As a result of the measurement, when the glycerin content relative to 100 parts by weight of the initial oil was 5.0-7.0 parts by weight (oil conversion rate: 40-60%), Lt; / RTI > The reaction was terminated when the initially introduced oil conversion rate was 98% while continuously maintaining the reactor pressure at 5 mmHg and the temperature was lowered to 50 ° C or lower to obtain 440 g of a fatty acid hydroxyalkylamine ester. 44 g of glycerin was obtained in a glycerine reservoir connected to the reactor.
The glycerin content was determined by GC analysis (TE90 carbon composition analysis method). In the reactor, 0.2 g of the sample was placed in a 100 ml separative funnel and dissolved by adding 1 ml of pyridine. 0.2 ml of hexamethyldisilazane (HMDS) and 0.1 ml of trimethylchlorosilane (TMCS) were added to the reaction mixture, and the stopper was closed, shaken vigorously, and the mixture was allowed to stand. Then, 10 ml of n-hexane was added and allowed to shake. It was also washed 4-5 times with 10% NaCl aqueous solution until no smell of pyridine was observed. The Hexane layer was dehydrated and filtered with anhydrous Na 2 SO 4 and GC analysis was performed under the following conditions.
Column: Non-polar Column 30m
Inlet temperature: 300 ° C
Detector temperature: 320 ° C
Oven temperature: 100 占 폚? 10 占 폚 / min? 320 占 폚 占 8 min
(2) Quaternization reaction
Was added to 440 g of the fatty acid hydroxyalkylamine ester obtained in the above step (1) in 65 g of isopropyl alcohol. Then, 90 g of dimethyl sulfate as a quaternizing agent was slowly dropped by one drop, quaternarized at 45-50 ° C for 3 hours, and 40 g of recovered glycerin was added to prepare ester quat.
(3) Manufacture of fabric softener
Using the prepared ester quat, a fabric softening agent was prepared as shown in Table 1 below.
≪ Example 2 >
Ester quat and a fabric softener were prepared in the same manner as in Example 1, except that 512 g of palmsteen oil was used in Example 1.
≪ Example 3 >
The ester quat and the fabric softening agent were prepared in the same manner as in Example 1 except that 512 g of palm olein oil was used in Example 1.
≪ Comparative Example 1 &
A fabric softener was prepared in the same manner as in Example 1 using PEQ90, which is a conventional ester quat.
≪ Comparative Example 2 &
A fabric softener was prepared by the same method as in Example 1 using MEQ manufactured by Ohseong Chemical Co.,
≪ Comparative Example 3 &
A fabric softening agent was prepared in the same manner as in Example 1 using Aekyung EEQ.
≪ Comparative Example 4 &
A fabric softener was prepared in the same manner as in Example 1 using Stepan SP90.
≪ Comparative Example 5 &
A fabric softener was prepared in the same manner as in Example 1 using Evonic Rewequad we15.
≪ Comparative Example 6 >
A fabric softener was prepared in the same manner as in Example 1 using a Cliant EQ product.
The fabric softeners prepared in Examples 1 to 3 and Comparative Examples 1 to 6 were measured for viscosity and long-term stability at 45 ° C and 60 ° C, respectively, and are shown in Tables 2 and 3, respectively. Viscosity measurements were made at Brookfield viscometer using Spindle # 63 at 20 rpm, and the stability test was done by the softener accelerated test method. Generally, incubation at 45 ℃ incubator is 8 weeks at room temperature, 1 year at 60 ℃ incubator, 4 weeks at room temperature and 1 year stability.
(cps)
(cps)
As shown in Tables 2 and 3, the ester quat and fabric softener prepared according to the present invention have remarkably improved viscosity and stability as compared with the fabric softener prepared using the conventional ester quart.
Claims (8)
Reacting the prepared fatty acid hydroxyalkylamine ester with a quaternizing agent in a solvent,
Wherein R < 1 > and R < 2 >
[Chemical Formula 1]
In Formula 1,
A and B are each independently CH 2 CH 2 OH or CH 2 CH 2 OCR 2 ,
R 1 and R 2 are each independently selected from the group consisting of C 11 -C 21 linear or branched alkyl, alkenyl, and combinations thereof. Process for the production of ester quats (EQ).
Wherein the secondary ester exchange reaction is performed at a lower pressure than the primary ester exchange reaction.
Wherein the reaction of the first ester exchange reaction is 10-50 mmHg, and the pressure of the second ester exchange reaction is 0-10 mmHg.
Wherein the organic solvent is isopropyl alcohol.
Wherein the viscosity of the final fabric softener is 300-600 cps without using the thickener during the mixing.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20120124094A KR20140070682A (en) | 2012-11-05 | 2012-11-05 | Esterquat and preparation method thereof |
| PCT/KR2013/009430 WO2014069833A1 (en) | 2012-11-05 | 2013-10-22 | Esterquat and method for preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20120124094A KR20140070682A (en) | 2012-11-05 | 2012-11-05 | Esterquat and preparation method thereof |
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| Publication Number | Publication Date |
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| KR20140070682A true KR20140070682A (en) | 2014-06-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR20120124094A KR20140070682A (en) | 2012-11-05 | 2012-11-05 | Esterquat and preparation method thereof |
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| KR (1) | KR20140070682A (en) |
| WO (1) | WO2014069833A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018048023A1 (en) * | 2016-09-08 | 2018-03-15 | 선진뷰티사이언스(주) | Fabric softening agent comprising tripropylene glycol solvent and method for producing same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112384601B (en) | 2018-07-11 | 2022-06-17 | 科莱恩国际有限公司 | Preparation and use of high quality esterquat derived from rice bran fatty acids |
| EP4274881A1 (en) | 2021-01-11 | 2023-11-15 | Clariant International Ltd | Hydrogenated esterquats from rice bran fatty acids and their preparation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2179757B1 (en) * | 2000-12-22 | 2003-12-16 | Kao Corp Sa | SOFTENING COMPOSITIONS OF FIBERS CONTAINING NON-IONIC TENSIOACTIVE. |
| KR100473765B1 (en) * | 2002-12-23 | 2005-03-10 | 주식회사 엘지생활건강 | Fabric softener composition |
| KR100968174B1 (en) * | 2008-12-09 | 2010-07-07 | 오성화학공업주식회사 | Preparation method of fabric softeners |
| KR101050726B1 (en) * | 2011-03-22 | 2011-07-20 | 주식회사 선진화학 | Fabric softener and preparation method thereof |
-
2012
- 2012-11-05 KR KR20120124094A patent/KR20140070682A/en not_active Application Discontinuation
-
2013
- 2013-10-22 WO PCT/KR2013/009430 patent/WO2014069833A1/en active Application Filing
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018048023A1 (en) * | 2016-09-08 | 2018-03-15 | 선진뷰티사이언스(주) | Fabric softening agent comprising tripropylene glycol solvent and method for producing same |
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| WO2014069833A1 (en) | 2014-05-08 |
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