CA2820583A1 - Composition lubrifiante contenant un agent ameliorant l'indice de viscosite - Google Patents
Composition lubrifiante contenant un agent ameliorant l'indice de viscosite Download PDFInfo
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- CA2820583A1 CA2820583A1 CA2820583A CA2820583A CA2820583A1 CA 2820583 A1 CA2820583 A1 CA 2820583A1 CA 2820583 A CA2820583 A CA 2820583A CA 2820583 A CA2820583 A CA 2820583A CA 2820583 A1 CA2820583 A1 CA 2820583A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 149
- 239000000314 lubricant Substances 0.000 title claims abstract description 83
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 18
- 239000003921 oil Substances 0.000 claims description 64
- 239000002270 dispersing agent Substances 0.000 claims description 48
- 239000003599 detergent Substances 0.000 claims description 43
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 26
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 230000001050 lubricating effect Effects 0.000 claims description 14
- 229960002317 succinimide Drugs 0.000 claims description 14
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 238000002485 combustion reaction Methods 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- 239000003607 modifier Substances 0.000 claims description 10
- 229920002367 Polyisobutene Polymers 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 5
- 230000000153 supplemental effect Effects 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000006078 metal deactivator Substances 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000000994 depressogenic effect Effects 0.000 claims description 2
- 230000008961 swelling Effects 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims 1
- -1 ethylene, propylene Chemical group 0.000 abstract description 49
- 235000019198 oils Nutrition 0.000 description 59
- 229910052751 metal Inorganic materials 0.000 description 33
- 239000002184 metal Substances 0.000 description 33
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
- 239000010705 motor oil Substances 0.000 description 19
- 239000002199 base oil Substances 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 229920000768 polyamine Polymers 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 229910052719 titanium Inorganic materials 0.000 description 10
- 239000010936 titanium Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000005266 diarylamine group Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000003900 succinic acid esters Chemical class 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 150000003609 titanium compounds Chemical class 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012968 metallocene catalyst Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 3
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 3
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 3
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- UNBOSJFEZZJZLR-UHFFFAOYSA-N 4-(4-nitrophenylazo)aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 UNBOSJFEZZJZLR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 102100037815 Fas apoptotic inhibitory molecule 3 Human genes 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 101000878510 Homo sapiens Fas apoptotic inhibitory molecule 3 Proteins 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
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- 239000004327 boric acid Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
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Abstract
La présente invention concerne des compositions lubrifiantes contenant des agents améliorant l'indice de viscosité sous forme de polymères comprenant des motifs structuraux dérivés de l'éthylène, du propylène et du butylène.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US42176410P | 2010-12-10 | 2010-12-10 | |
US61/421,764 | 2010-12-10 | ||
PCT/US2011/063425 WO2012078572A1 (fr) | 2010-12-10 | 2011-12-06 | Composition lubrifiante contenant un agent améliorant l'indice de viscosité |
Publications (2)
Publication Number | Publication Date |
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CA2820583A1 true CA2820583A1 (fr) | 2012-06-14 |
CA2820583C CA2820583C (fr) | 2018-10-30 |
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ID=45401165
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2820583A Active CA2820583C (fr) | 2010-12-10 | 2011-12-06 | Composition lubrifiante contenant un agent ameliorant l'indice de viscosite |
Country Status (9)
Country | Link |
---|---|
US (1) | US20140005086A1 (fr) |
EP (1) | EP2649167B1 (fr) |
JP (1) | JP5897030B2 (fr) |
KR (1) | KR101815338B1 (fr) |
CN (1) | CN103354832B (fr) |
BR (1) | BR112013014297A2 (fr) |
CA (1) | CA2820583C (fr) |
SG (1) | SG190994A1 (fr) |
WO (1) | WO2012078572A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2924890C (fr) * | 2013-09-19 | 2022-03-22 | The Lubrizol Corporation | Compositions lubrifiantes pour moteurs a injection directe |
WO2015042341A1 (fr) * | 2013-09-19 | 2015-03-26 | The Lubrizol Corporation | Compositions lubrifiantes pour moteurs à injection directe |
JP2016534216A (ja) * | 2013-09-19 | 2016-11-04 | ザ ルブリゾル コーポレイションThe Lubrizol Corporation | 直噴エンジン用潤滑剤組成物 |
CN103468352A (zh) * | 2013-09-26 | 2013-12-25 | 麦特汽车服务股份有限公司 | 一种发动机保护剂 |
CN106459814B (zh) * | 2015-03-24 | 2021-04-06 | 出光兴产株式会社 | 汽油发动机用润滑油组合物及其制造方法 |
CN108641790A (zh) * | 2018-04-28 | 2018-10-12 | 山东源根化学技术研发有限公司 | 一种燃气发动机润滑油组合物及其制备方法 |
EP3950897A4 (fr) * | 2019-03-26 | 2022-08-10 | Mitsui Chemicals, Inc. | Composition d'huile lubrifiante pour huile de compresseur, et procédé de fabrication de celle-ci |
JP7219663B2 (ja) * | 2019-04-16 | 2023-02-08 | 三井化学株式会社 | 潤滑油用粘度調整剤および潤滑油組成物 |
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DE1595234A1 (de) | 1965-04-27 | 1970-03-05 | Roehm & Haas Gmbh | Verfahren zur Herstellung oligomerer bzw. polymerer Amine |
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-
2011
- 2011-12-06 CN CN201180067197.5A patent/CN103354832B/zh active Active
- 2011-12-06 WO PCT/US2011/063425 patent/WO2012078572A1/fr active Application Filing
- 2011-12-06 JP JP2013543249A patent/JP5897030B2/ja active Active
- 2011-12-06 EP EP11799913.6A patent/EP2649167B1/fr active Active
- 2011-12-06 SG SG2013043146A patent/SG190994A1/en unknown
- 2011-12-06 KR KR1020137017069A patent/KR101815338B1/ko active IP Right Grant
- 2011-12-06 BR BR112013014297A patent/BR112013014297A2/pt not_active Application Discontinuation
- 2011-12-06 CA CA2820583A patent/CA2820583C/fr active Active
- 2011-12-06 US US13/991,707 patent/US20140005086A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP2649167B1 (fr) | 2016-03-09 |
WO2012078572A1 (fr) | 2012-06-14 |
EP2649167A1 (fr) | 2013-10-16 |
JP5897030B2 (ja) | 2016-03-30 |
CA2820583C (fr) | 2018-10-30 |
KR20130130003A (ko) | 2013-11-29 |
CN103354832A (zh) | 2013-10-16 |
KR101815338B1 (ko) | 2018-01-30 |
BR112013014297A2 (pt) | 2016-09-20 |
JP2013544948A (ja) | 2013-12-19 |
US20140005086A1 (en) | 2014-01-02 |
CN103354832B (zh) | 2015-11-25 |
SG190994A1 (en) | 2013-07-31 |
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