WO2010080019A2 - Refining of edible oil - Google Patents

Refining of edible oil Download PDF

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Publication number
WO2010080019A2
WO2010080019A2 PCT/MY2009/000224 MY2009000224W WO2010080019A2 WO 2010080019 A2 WO2010080019 A2 WO 2010080019A2 MY 2009000224 W MY2009000224 W MY 2009000224W WO 2010080019 A2 WO2010080019 A2 WO 2010080019A2
Authority
WO
WIPO (PCT)
Prior art keywords
palm oil
liquid fraction
free fatty
refined
oil
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.)
Ceased
Application number
PCT/MY2009/000224
Other languages
English (en)
French (fr)
Other versions
WO2010080019A3 (en
Inventor
Khairuddin Hashim
Mohd Suria Affandi Yusoff
Razam Abd Latip
Ananthan Krishnan
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.)
Sime Darby Research Sdn Bhd
Original Assignee
Sime Darby Research Sdn Bhd
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 Sime Darby Research Sdn Bhd filed Critical Sime Darby Research Sdn Bhd
Priority to EP09837690.8A priority Critical patent/EP2373177A4/en
Priority to US13/142,672 priority patent/US8716505B2/en
Priority to JP2011545309A priority patent/JP5827568B2/ja
Publication of WO2010080019A2 publication Critical patent/WO2010080019A2/en
Publication of WO2010080019A3 publication Critical patent/WO2010080019A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0075Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00Refining fats or fatty oils
    • C11B3/001Refining fats or fatty oils by a combination of two or more of the means hereafter
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00Refining fats or fatty oils
    • C11B3/006Refining fats or fatty oils by extraction
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00Refining fats or fatty oils
    • C11B3/02Refining fats or fatty oils by chemical reaction
    • C11B3/04Refining fats or fatty oils by chemical reaction with acids
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00Refining fats or fatty oils
    • C11B3/02Refining fats or fatty oils by chemical reaction
    • C11B3/06Refining fats or fatty oils by chemical reaction with bases
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00Refining fats or fatty oils
    • C11B3/12Refining fats or fatty oils by distillation

Definitions

  • the present invention relates to a process of refining edible oil rich in natural occurring carotene. More particularly, the present invention relates to a process of refining palm oil whereby substantially a large amount of the naturally occurring carotene is retained in the refined oil.
  • Carotenes are yellow to orange pigments found in carrots, leafy vegetables, milk fat and egg yolk.
  • the a- and b-carotenes are associated with synthesis of vitamin A in the liver and may offer some protection against cancer as well.
  • the refined oil of the prior art process normally has a free fatty acid (FFA) content of less than 0.1%, carotene content of less than 20 ppm and colour of less than 3 red in a 5 1/4" cell (Lovibond Scale).
  • FFA free fatty acid
  • Prior art refining process of crude palm oil in summary involve deodorizing at temperatures between 24O 0 C - 260 0 C and at a pressure of 0.1 - 0.4 kPa, which result in not only the removal of unwanted fatty acids but also all carotenes being destroyed.
  • Alpha ( ⁇ ), beta ( ⁇ ), gamma (y) and zeta ( ⁇ ), zeacarotene, cis a-carotene, cis b-carotene and lycopene are destroyed.
  • degassing of the crude palm oil and deodorizing of the degassed oil is done within the same equipment.
  • the typical operating temperature is between 240 0 C and 260 0 C.
  • FFA free fatty acids
  • AU-B-31084189 discloses an improved process for the refining of edible palm oil substantially without destroying the carotenes present in the oil which process comprises the step of subjecting the oil to a pressure of less than 0.008 kPa and a temperature of less than 200 0 C.
  • palm oil or a product of palm oil is passed through a deodorizer, preferably at a temperature in the range 100 0 C to 200°C and at a pressure of up to 0.008 kPa.
  • a deodorizer preferably at a temperature in the range 100 0 C to 200°C and at a pressure of up to 0.008 kPa.
  • This deodorized palm oil has a free fatty acid content of less than 0.12%.
  • MY-124490-A discloses modifications to conventional process of refining crude palm oil so that carotene content is substantially retained but devoid of other impurities.
  • the modifications comprise (i) repeating neutralization step at least once at 80 0 C to remove free fatty acids from the palm oil; (ii) removing the remaining free fatty acid and other impurities by deodorization at relatively low temperatures, i.e. about 150°C; and (iii) crystallizing and fractionating the palm oil at relatively low temperature, i.e.
  • the refined palm oil contains less than 0.1% free fatty acid, has a carotene content retained of about 70%, a cloud point of less than 10 0 C and an iodine value of more than 60.
  • the above-mentioned Malaysian patent has several disadvantages.
  • the refined palm oil contains high amount of peroxides which deteriorates the quality of the oil.
  • the oil undergoes fractionation, whereby the oil is heated up to 65 0 C. This leads to an increase of peroxides in the final product or refined oil, which deteriorates quality of the refined oil as time passes.
  • repetition of neutralization step incurs more oil losses, thus reducing the yield of the final product (i.e. refined palm oil).
  • Repetition of the neutralization step of at least once also increases the cost of production.
  • gel-like partial glyceride is formed during deodorisation, which makes it difficult to filter the oil during the fractionation and crystallization step. Thus, the entire refining process has to be repeated.
  • the present invention discloses a commercial process for the production of refined palm oil rich in natural carotene.
  • the process for the production of natural carotene rich refined oil comprises the steps of: (a) fractionating crude palm oil to form a liquid fraction and a solid portion;
  • step (f) deodorizing the neutralized product of step (e) to remove remaining free fatty acids and other impurities contained therein, thus forming a refined palm oil that contains less than 0.1 % free fatty acid, has a carotene content retained of about 75%, an iodine value of less than 60 and a peroxide value of zero.
  • the fractionation step of the present process includes heating the palm oil to 70°C for 15 minutes with constant and homogenizing stirring, followed by cooling to 19°C so that the solid portion (i.e. stearin and other solid fats) of the oil is separated from the liquid fraction (i.e. olein).
  • liquid fraction (olein) and the solid portion (stearin and other solid fats) of the fractionated crude palm oil may be easily separated using physical means such as vacuum or press-type filters.
  • the neutralization step of the present process is carried out at a temperature lower than 85°C.
  • the preferred neutralization temperature is 65°C.
  • the deodorizing step of the present process is carried out at 155°C to 165 C C in a vacuum vessel for 4.5 to 5.5 hours. Preferably, deodorization is carried out at 160 0 C for 5 hours.
  • This deodorization step eliminates the presence of peroxides in the resultant refined palm oil, which increased after the fractionation step. By eliminating peroxides entirely, the resultant refined palm oil is considered to be of high quality containing less than 0.1 % free fatty acid.
  • the process does not involve expensive equipments such as distiller and condenser. Further, the steps involved are simple and do not involve much cost. For example, neutralization step need not be repeated more than once as required in the prior art. Thus, the cost of production and oil losses can be minimized in the present process.
  • deodorization induces the formation of gel-like partial glyceride, which makes it difficult for the oil to be filtered during the subsequent step of fractionation, thus requiring the whole process to be repeated.
  • the present process solves this problem by introducing fractionation of crude palm oil as the first step.
  • formation of gel-like partial glyceride during the last step of deodorization in the present invention does not possess a problem that will require the process to be repeated because the resultant refined palm oil is not subject to filtration.
  • the crude palm oil is first subjected to fractionation to remove high melting point solids. This is performed at relatively low temperature to ensure the palm oil remains clear for a longer period of time.
  • the crude palm oil is heated at about 70 0 C for approximately 15 minutes with constant and homogenizing stirring. It is then cooled slowly to 19°C using, for example an external flow of cooling water. At this low temperature, the liquid is separated from the solids, i.e. the remaining stearins and solid fats.
  • the separation of liquid palm oil, called crude palm olein (still in red colour), from stearin may be carried out using vacuum or press-type filters.
  • fractionated liquid palm oil (or palm olein) is then degummed with concentrated phosphoric acid at temperatures below 100 0 C for a period of 10 to 30 minutes.
  • degumming is carried out at below 85°C for a period of 15 minutes.
  • the degummed liquid palm oil (or palm olein) is further neutralized with concentrated alkali, such as sodium hydroxide. This step is carried out at a temperature below 85°C for a period of 15 minutes. It is preferred that neutralization is carried out at a temperature of 65°C.
  • the amount of alkali used depends on the level of free fatty acid present in the degummed oil. Soap formed as a result of the neutralization reaction is removed from the liquid palm oil (or palm olein) by watering-washing. The palm olein is washed with water until no traces of soap can be found.
  • the neutralized liquid palm oil (or palm olein) is deodorized at an elevated temperature ranging from 155°C to 165°C in a vacuum vessel for a period of 4.5 to 5.5 hours.
  • deodorization is carried out at 160 0 C in a vacuum vessel for a period of 5 hours. It would be understood to a person skilled in the art that absolute vacuum may not be achievable in an ordinary or industrial vacuum vessel and therefore, there is usually a presence of small residue of pressure of 130 kPa.
  • the resultant refined palm oil is still red in colour indicating that the carotene content is substantially retained. It contains less than 0.1% free fatty acid, has a carotene content retained of about 75%, an iodine value of less than 60 and a peroxide value of zero.
  • Crude palm oil was subjected to fractionation to remove high melting point solids. Crude was heated to about 70 0 C for 15 minutes with constant and homogenizing stirring. It is then cooled slowly by external cool water to 19°C so that the liquid fraction is separated from the solid portion, which consists of the remaining stearin and solid fats.
  • the liquid palm oil called crude palm olein (still in red colour) was separated from the solid portion by way of vacuum or press-type filter.
  • the crude palm olein is then degummed using 0.04% by volume of 85% phosphoric acid at a temperature below 85°C for 15 minutes.
  • the degummed palm olein is then neutralized with 4N sodium hydroxide solution at 65°C.
  • the soap formed as a result of the neutralization reaction is removed from the palm olein by washing with water until no traces of soap can be found.
  • the neutralized palm olein is then deodorized at 160 c C in a vacuum vessel for 5 hours. Residue pressure was recorded at 130 kPa.
  • the final refined palm oil contained less than 0.1 % free fatty acid, has a carotene content retained of about 75%, an iodine value of less than 60 and a peroxide value of zero.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)
PCT/MY2009/000224 2009-01-08 2009-12-31 Refining of edible oil Ceased WO2010080019A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP09837690.8A EP2373177A4 (en) 2009-01-08 2009-12-31 REFINEMENT OF EDIBLE OIL
US13/142,672 US8716505B2 (en) 2009-01-08 2009-12-31 Refining of edible oil
JP2011545309A JP5827568B2 (ja) 2009-01-08 2009-12-31 食用油の精製

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
MYPI20090069 2009-01-08
MYPI20090069A MY188429A (en) 2009-01-08 2009-01-08 Refining of edible oil

Publications (2)

Publication Number Publication Date
WO2010080019A2 true WO2010080019A2 (en) 2010-07-15
WO2010080019A3 WO2010080019A3 (en) 2010-10-28

Family

ID=42317028

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/MY2009/000224 Ceased WO2010080019A2 (en) 2009-01-08 2009-12-31 Refining of edible oil

Country Status (5)

Country Link
US (1) US8716505B2 (enExample)
EP (1) EP2373177A4 (enExample)
JP (1) JP5827568B2 (enExample)
MY (1) MY188429A (enExample)
WO (1) WO2010080019A2 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014000012A (ja) * 2012-06-15 2014-01-09 Ueda Oils & Fats Mfg Co Ltd 食用油脂の製造方法
EP2611767B1 (en) 2010-09-03 2017-10-25 Stepan Specialty Products, LLC Elimination of organohalo and oxirane species in carboxylic acid ester streams
WO2019147121A1 (en) * 2018-01-26 2019-08-01 Sime Darby Plantation Intellectual Property Sdn. Bhd. Process for producing cold pressed palm fruit oil

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6050037B2 (ja) * 2012-06-29 2016-12-21 株式会社J−オイルミルズ 油脂組成物、それを利用した食品、油脂組成物の製造方法及び食用油脂の光劣化抑制方法
US9889084B2 (en) * 2014-01-10 2018-02-13 Valicor, Inc. Compositions of cosmetic, personal care and skin care products derived from lipid feedstocks and methods to produce the same
CN107557149A (zh) * 2016-06-30 2018-01-09 吴忠市兴达粮油有限公司 一种胡麻油毛油精炼工艺
CN107574013A (zh) * 2016-07-04 2018-01-12 吴忠市兴达粮油有限公司 一种棉籽油精炼脱毒提取工艺
JP6246883B2 (ja) * 2016-11-22 2017-12-13 株式会社J−オイルミルズ 食用油脂中での異風味の抑制方法
SG11202104013WA (en) * 2018-10-31 2021-05-28 J Oil Mills Inc Oxidized product of palm-based oil and fat, method for producing oxidized product, method for enhancing food sweetness, and composition for enhancing food sweetness
WO2020209158A1 (ja) * 2019-04-11 2020-10-15 株式会社J-オイルミルズ 食品用油脂感増強剤及び食品の油脂感増強方法
US20220361519A1 (en) * 2019-09-30 2022-11-17 J-Oil Mills, Inc. Umami-enhancing composition and method for manufacturing same, seasoning or extract and method for manufacturing same, oil and fat composition for cooking with heat and method for manufacturing same, and method for enhancing umami of food product
WO2021153310A1 (ja) * 2020-01-31 2021-08-05 株式会社J-オイルミルズ カロテノイド分解物を有効成分とする塩味増強剤
WO2021153309A1 (ja) * 2020-01-31 2021-08-05 株式会社J-オイルミルズ カロテノイド分解物を有効成分とする苦味抑制剤
JP7668236B2 (ja) * 2020-01-31 2025-04-24 株式会社J-オイルミルズ カロテノイド分解物を有効成分とする酸味抑制剤
JP7637514B2 (ja) * 2021-01-25 2025-02-28 株式会社ニップン カルボナーラ風ソース
JP7752978B2 (ja) * 2021-06-30 2025-10-14 太陽油脂株式会社 加熱調理用油脂組成物及びその製造方法
JP7784833B2 (ja) * 2021-07-01 2025-12-12 株式会社J-オイルミルズ 食品用酸臭抑制剤
CN113846130B (zh) * 2021-09-18 2024-03-01 江南大学 一种c52结构脂的酶法合成方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB700400A (en) * 1951-09-28 1953-12-02 Inst Rech S Pour Les Huiles De Method of producing high-value carotene-containing palm oil from palm-tree waste products
US3632616A (en) * 1968-04-24 1972-01-04 Richard Kassabian Apparatus and process for the selective fractionation of fatty materials into useful fractions thereof
JPS5271509A (en) * 1975-12-11 1977-06-15 Asahi Denka Kogyo Kk Purification of palm oil
AU632272B2 (en) 1988-03-11 1992-12-24 Malaysian Palm Oil Board Refining of edible oil
JPH07247495A (ja) * 1994-03-09 1995-09-26 Fuji Oil Co Ltd 高カロテン含有油脂の製造法
MY124490A (en) 1996-01-15 2006-06-30 Malaysian Palm Oil Board High carotene palm oil production by repeated neutralisation and low temperature deodorisation
US6177114B1 (en) * 1996-10-31 2001-01-23 Carotina Sdn. Bhd. Refining of edible oil rich in natural carotenes and Vitamin E
MY127634A (en) * 1996-10-31 2006-12-29 Global Palm Products Sdn Bhd Refining of edible oil rich in natural carotenes and vitamin e
MY146635A (en) * 2004-09-01 2012-09-14 Malaysian Palm Oil Board Specialty palm oil products and other specialty vegetable oil products
DE602006013933D1 (de) * 2006-02-10 2010-06-10 Carotech Sdn Bhd Chemor Verfahren zur Gewinnung hochangereicherter Naturstoff-fraktionen aus Palmöl unter Verwendung von superkritischen und beinahe superkritischen Flüssigmedien

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2373177A4 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2611767B1 (en) 2010-09-03 2017-10-25 Stepan Specialty Products, LLC Elimination of organohalo and oxirane species in carboxylic acid ester streams
USRE48861E1 (en) 2010-09-03 2021-12-28 Stepan Specialty Products, Llc Elimination of organohalo and oxirane species in carboxylic acid ester streams
JP2014000012A (ja) * 2012-06-15 2014-01-09 Ueda Oils & Fats Mfg Co Ltd 食用油脂の製造方法
WO2019147121A1 (en) * 2018-01-26 2019-08-01 Sime Darby Plantation Intellectual Property Sdn. Bhd. Process for producing cold pressed palm fruit oil

Also Published As

Publication number Publication date
WO2010080019A3 (en) 2010-10-28
US20110275843A1 (en) 2011-11-10
MY188429A (en) 2021-12-08
EP2373177A2 (en) 2011-10-12
JP5827568B2 (ja) 2015-12-02
US8716505B2 (en) 2014-05-06
JP2012514470A (ja) 2012-06-28
EP2373177A4 (en) 2016-06-15

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