CN105229125B - 具有增强能量效率的润滑油组合物 - Google Patents
具有增强能量效率的润滑油组合物 Download PDFInfo
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- CN105229125B CN105229125B CN201480026817.4A CN201480026817A CN105229125B CN 105229125 B CN105229125 B CN 105229125B CN 201480026817 A CN201480026817 A CN 201480026817A CN 105229125 B CN105229125 B CN 105229125B
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- Prior art keywords
- acid
- single methanol
- lubricant oil
- weight
- oil composite
- Prior art date
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- 239000000314 lubricant Substances 0.000 title claims abstract description 52
- 239000002131 composite material Substances 0.000 title claims abstract description 32
- 230000002708 enhancing effect Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000005461 lubrication Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 114
- -1 2- methyl-butvl, 3- methyl-butvl Chemical class 0.000 claims description 68
- 239000003921 oil Substances 0.000 claims description 63
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 14
- 239000001361 adipic acid Substances 0.000 claims description 13
- 235000011037 adipic acid Nutrition 0.000 claims description 13
- 229920013639 polyalphaolefin Polymers 0.000 claims description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 10
- 230000001050 lubricating effect Effects 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 7
- 239000010687 lubricating oil Substances 0.000 claims description 7
- 239000002480 mineral oil Substances 0.000 claims description 7
- 235000010446 mineral oil Nutrition 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
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- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 claims description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- HDLHSQWNJQGDLM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,5-dicarboxylic acid Chemical class C1C2C(C(=O)O)CC1C(C(O)=O)C2 HDLHSQWNJQGDLM-UHFFFAOYSA-N 0.000 claims description 3
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 claims description 3
- 235000011087 fumaric acid Nutrition 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
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- 239000004327 boric acid Substances 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 16
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 16
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 13
- 238000005885 boration reaction Methods 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 9
- 229910052796 boron Inorganic materials 0.000 description 9
- 239000005864 Sulphur Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000003925 fat Substances 0.000 description 8
- 235000019197 fats Nutrition 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 229960002317 succinimide Drugs 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000010705 motor oil Substances 0.000 description 7
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 5
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- 150000001721 carbon Chemical group 0.000 description 5
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- 239000010725 compressor oil Substances 0.000 description 5
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
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- 239000003112 inhibitor Substances 0.000 description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
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- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical class S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
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- 239000007859 condensation product Substances 0.000 description 4
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- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
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Abstract
本发明涉及在机械装置的润滑中降低润滑油组合物的摩擦系数的方法，其包括用可通过使包含至少一种二羧酸和至少一种支化C10醇的混合物反应而得到的羧酸酯配制所述润滑油组合物。
Description
本发明涉及在机械装置的润滑中降低润滑油组合物的摩擦系数的方法，其包括用可通过使包含至少一种二羧酸和至少一种支化C10醇的混合物反应而得到的羧酸酯配制所述润滑油组合物。
市售润滑油组合物由多种不同的天然或合成组分制备。为改进所需性能，根据使用领域，通常加入其它添加剂。基油通常由矿物油、高精炼矿物油、烷基化矿物油、聚-α-烯烃(PAO)、聚亚烷基二醇、磷酸酯、硅油、二酯和多元醇酯组成。
不同的润滑剂，例如发动机油、涡轮机油、液压流体、变速器用油、压缩机油等必须满足极高的标准，例如高粘度指数、良好的润滑剂性能、高氧化稳定性、良好的热稳定性或相当的性能。
用作变速器、工业或发动机油的高性能润滑油配制剂为具有在剪切稳定性、低温粘度、长使用寿命、蒸发损失、燃料效率、密封相容性和磨损保护方面的特殊性能特征的油。除常规添加剂组分外，这类油目前优选用PAO(尤其是PAO 6)或者第I、II或III组矿物油作为载液，并且用特殊聚合物(聚异丁烯＝PIB，烯烃共聚物＝乙烯/丙烯共聚物＝OCP，聚甲基丙烯酸烷基酯＝PMA)作为增稠剂或粘度指数改进剂配制。与PAO一起，低粘度酯通常使用例如DIDA(己二酸二异癸酯)、DITA(己二酸二-异十三烷基酯)或TMTC(三羟甲基丙烷辛酸酯)，尤其是作为极性添加剂类型的增溶剂和用于使密封相容性最佳化。
酯作为助溶剂尤其用于发动机油、涡轮机油、液压流体、变速器用油、压缩机油，但酯也用作基油，其中它们为主要组分。
EP 0 767 236 Al公开了一种齿轮润滑油组合物。该组合物含有大于20体积％氢化聚α-烯烃和小于80体积％矿物油或合成酯油或其组合。实例含有10体积％己二酸双(十三烷基)酯。
WO 98/04658 A1公开了用于重型和中型车轴齿轮润滑剂和传动流体应用中的合成齿轮油用基本油料。此处公开的润滑剂含有1-20重量％酯。该酯包括C8-13己二酸酯的二酯，特别是己二酸二-异癸酯。
美国专利4,370,247公开了含有25-60质量％至少一种二羧酸的二-C8-12烷基酯的齿轮或车轴润滑剂。报告了此处公开的整个润滑剂降低了由于摩擦导致的功率损耗，因此保持燃料消耗。
CA 2 637 401公开了衍生自具有2-36个碳原子的二羧酸和具有4-40个碳原子的支化醇的多种二酯。该润滑剂可含有0.1-100重量％或5-99重量％二酯。
WO 2011/34829 A1公开了润滑限滑差速器的方法，其包括向限滑差速器中供入包含己二酸的C4-30二酯的润滑组合物。
尽管不同的润滑剂，例如发动机油、涡轮机油、液压流体、变速器用油、压缩机油等满足极高的标准，例如高粘度指数、良好的润滑剂性能、高氧化稳定性和良好热稳定性，仍需要降低机械装置操作期间消耗的能量。
因此，本发明的目的是提供容许以较低的能量消耗操作机械装置的方法。
该目的通过提供在机械装置的润滑中降低润滑油组合物的摩擦系数的方法而实现，所述方法包括用可通过使包含以下组分的混合物反应而得到的羧酸酯配制所述润滑油组合物：
a)至少一种二羧酸，任选为其酐的形式，和
b1)至少一种具有10个碳原子和通式I结构的单醇：
其中R1为戊基，R2为H且R3为丙基。
在本发明意义上，术语润滑油组合物意指能够降低移动表面之间的摩擦的物质。
摩擦改进性能通过使用微牵引力测定仪(MTM)测量在70℃和1GPa下以25％滑滚比(SRR)测量摩擦系数而测定。
在本发明意义上，降低摩擦系数意指包含如上所述羧酸酯的润滑油组合物的摩擦系数低于不包含所述羧酸酯的润滑油组合物的摩擦系数。
在本发明意义上，机械装置为由基于机械原理工作的装置组成的机制。
优选，二羧酸选自邻苯二甲酸、琥珀酸、烷基琥珀酸和烯基琥珀酸、马来酸、壬二酸、辛二酸、癸二酸、富马酸、己二酸、亚油酸二聚物、丙二酸、烷基丙二酸、烯基丙二酸、戊二酸、二甘醇酸、1,4-环己烷二羧酸、2,6-十氢化萘二羧酸、1,3-环己烷二羧酸和2,5-降莰烷二羧酸。更优选，二羧酸选自戊二酸、二甘醇酸、琥珀酸、壬二酸、癸二酸、1,4-环己烷二羧酸、己二酸、2,6-十氢化萘二羧酸、1,3-环己烷二羧酸和2,5-降莰烷二羧酸。最优选，脂族二羧酸为己二酸。
二羧酸可以以纯形式或者以与单羧酸的混合物的形式使用。代替二羧酸，也可使用它们的酐。代表性单羧酸包括正丁酸、正戊酸、正己酸、正庚酸、正辛酸、正壬酸、正癸酸、异丁酸、异戊酸、异己酸、异庚酸、异辛酸、2-乙基己酸、异壬酸、3,5,5-三甲基己酸和异癸酸。
优选，混合物进一步包含具有10个碳原子和通式II结构的单醇b2)：
其中：
R4选自戊基、异戊基、2-甲基-丁基、3-甲基-丁基和2,2-二甲基-丙基，
R5为H或甲基，且
R6选自乙基、丙基和异丙基，
其中单醇b1)和单醇b2)具有不同的结构。
优选，单醇b2)选自2-丙基-4-甲基-己醇、2-丙基-5-甲基-己醇、2-异丙基-4-甲基-己醇、2-异丙基-5-甲基-己醇、2-丙基-4,4-二甲基戊醇、2-乙基-2,4-二甲基己醇、2-乙基-2-甲基-庚醇、2-乙基-2,5-二甲基己醇和2-异丙基-庚醇。更优选，单醇b2)为2-丙基-4-甲基-己醇。
优选，单醇b1)与单醇b2)的重量比为5:1-95:1，更优选6:1-50:1，甚至更优选10:1-40:1，最优选20:1-35:1。
优选，混合物进一步包含具有10个碳原子和通式III结构的单醇b3)：
其中：
R7选自戊基、异戊基、2-甲基-丁基、3-甲基-丁基和2,2-二甲基-丙基，
R8为H或甲基，
R9选自乙基、丙基和异丙基。
优选，单醇b3)具有与单醇b1)和单醇b2)不同的结构。优选，单醇b3)选自2-丙基-5-甲基-己醇、2-异丙基-4-甲基-己醇、2-异丙基-5-甲基-己醇、2-丙基-4,4-二甲基戊醇、2-乙基-2,4-二甲基己醇、2-乙基-2-甲基-庚醇、2-乙基-2,5-二甲基己醇和2-异丙基-庚醇。更优选，单醇b3)为2-丙基-5-甲基-己醇。
优选，混合物包含80-95重量％2-正丙基-庚醇作为组分b1)，1.0-10重量％2-丙基-4-甲基-己醇作为组分b2)，1.0-10重量％2-丙基-5-甲基-己醇作为组分b3)和0.1-2.0重量％2-异丙基-庚醇，其中各组分的重量涉及单醇的总重量。更优选，混合物包含91.0-95.0重量％2-正丙基-庚醇作为组分b1)，2.0-5.0重量％2-丙基-4-甲基-己醇作为组分b2)，3.0-5.0重量％2-丙基-5-甲基-己醇作为组分b3)和0.1-0.8重量％2-异丙基-庚醇，其中各组分的重量涉及单醇的总重量。
优选，单醇b1)以相对于酸a)为2.05:1-3.0:1，更优选2.1:1-2.5:1的摩尔比存在。
优选，润滑油组合物包含相对于润滑油组合物的总量≥1％至≤10重量％或者≥1％至≤40重量％或者≥20％至≤100重量％，更优选≥1％至≤5重量％或者≥1％至≤35重量％或者≥25％至≤100重量％，最优选≥1％至≤2重量％或者≥2％至≤30重量％或者≥30％至≤100重量％的至少一种如上文所定义的羧酸酯。
优选，润滑油组合物进一步包含选自矿物油(第I、II或III组油)、聚α烯烃、聚合和共聚烯烃、烷基萘、氧化烯聚合物、硅油、磷酸酯和羧酸酯的其它基本油料。优选，润滑油包含相对于润滑油组合物的总量≥50％至≤99重量％或者≥80％至≤99重量％或者≥90％至≤99重量％基本油料。
本发明中关于基本油料的定义与American Petroleum Institute(API)出版物“Engine Oil Licensing and Certification System”，lndustry Services Department，第14版，1996年12月，附录1，1998年12月中找到的那些相同。所述出版物将基本油料如下分类：
a)使用下表所述试验方法，第I组基本油料包含小于90％饱和物和/或大于0.03％硫，且具有大于或等于80且小于120的粘度指数，
b)使用下表所述试验方法，第II组基本油料包含大于或等于90％饱和物和小于或等于0.03％硫，且具有大于或等于80且小于120的粘度指数，
c)使用下表所述试验方法，第III组基本油料包含大于或等于90％饱和物和小于或等于0.03％硫，且具有大于或等于120的粘度指数。
基本油料的分析方法
| 性能 | 测试方法 |
| 饱和物 | ASTM D 2007 |
| 粘度指数 | ASTM D 2270 |
| 硫 | ASTM D 2622 |
| ASTM D 4294 | |
| ASTM D 4927 | |
| ASTM D 3120 |
适于本发明的合成较低粘度流体包括聚α烯烃(PAO)以及来自费托高沸点馏分，包括蜡的加氢裂化或加氢异构化的合成油。这些为包含与其合成来源一致具有低杂质含量的饱和物的原料。加氢异构化费托合成蜡为非常合适的基本油料，其包含具有异链烷烃性质的饱和组分(由费托合成蜡的主要正链烷烃的异构化产生)，这赋予高粘度指数和低倾点的良好混合。费托合成蜡的加氢异构化方法描述于美国专利5,362,378；5,565,086；5,246,566和5,135,638以及EP 710710、EP 321302和EP 321304中。
适于本发明的聚α烯烃取决于其具体性能作为较低粘度或高粘度流体包括已知的PAO材料，其通常包含α烯烃的较低分子量氢化聚合物或低聚物，所述α烯烃包括但不限于C2至约C32α烯烃，其中优选C8至约C16α烯烃，例如1-辛烯、1-癸烯、1-十二碳烯等。优选的聚α烯烃为聚-1-辛烯、聚-1-癸烯和聚-1-十二碳烯，但C14-C18范围内的较高烯烃的二聚物提供低粘度基本油料。
适于本发明的低粘度PAO流体可方便地通过α烯烃在聚合催化剂如Friedel-Crafts催化剂，包括例如三氯化铝、三氟化硼或者三氟化硼与水、醇如乙醇、丙醇或丁醇、羧酸或酯如乙酸乙酯或丙酸乙酯的络合物的存在下聚合而制备。例如，美国专利4,149,178或3,382,291公开的方法可方便地用于本文中。关于PAO合成的其它描述在以下美国专利中找到：3,742,082(Brennan)；3,769,363(Brennan)；3,876,720(Heilman)；4,239,930(Allphin)；4,367,352(Watts)；4,413,156(Watts)；4,434,408(Larkin)；4,910,355(Shubkin)；4,956,122(Watts)；和5,068,487(Theriot)。
合成润滑油包括烃油和卤素取代烃油，例如聚合和共聚烯烃(例如聚丁烯、聚丙烯、丙烯-异丁烯共聚物、氯化聚丁烯、聚(1-己烯)、聚(1-辛烯)、聚(1-癸烯))；烷基苯(例如十二烷基苯、十四烷基苯、二壬基苯、二(2-乙基己基)苯)；聚苯(例如联苯、三联苯、烷基化多酚)；和烷基化二苯醚和烷基化二苯硫醚及其衍生物、类似物和同系物。
适于本发明的其它羧酸酯包括单和多元酸与单醇(简单酯)或者与单和多元醇的混合物(混合酯)的酯，以及单羧酸(简单酯)或者单和聚羧酸的混合物(混合酯)的多元醇酯。一元/多元类型的酯可包括例如单羧酸如庚酸和二羧酸如邻苯二甲酸、琥珀酸、烷基琥珀酸、烯基琥珀酸、马来酸、壬二酸、辛二酸、癸二酸、富马酸、己二酸、亚油酸二聚物、丙二酸、烷基丙二酸、烯基丙二酸等与多种醇如丁醇、己醇、十二醇、2-乙基己醇或其与多元醇的混合物的酯。这些类型的酯的具体实例包括庚酸壬酯、己二酸二丁酯、癸二酸二(2-乙基己基)酯、富马酸二-己基酯、癸二酸二辛酯、壬二酸二异辛酯、壬二酸二异癸酯、邻苯二甲酸二辛酯、邻苯二甲酸二癸酯、癸二酸二-二十烷基酯、TMP-己二酸二丁酯等。
适于本发明的还有酯，例如通过使一种或多种多元醇，优选受阻多元醇，例如新戊基多元醇如新戊二醇、三羟甲基乙烷、2-甲基-2-丙基-1,3-丙二醇、三羟甲基丙烷、三羟甲基丁烷、季戊四醇和二季戊四醇与包含至少4个碳的单羧酸，通常C5-C30酸如饱和直链脂肪酸，包括辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸和山萮酸，或者相应的支链脂肪酸或不饱和脂肪酸如油酸或其混合物与聚羧酸反应而得到的那些。
其中末端羟基通过酯化、醚化等改性的氧化烯聚合物和共聚物及其衍生物构成另一类已知的合成润滑油。这些通过如下例证：通过氧化乙烯或氧化丙烯聚合制备的聚氧化烯聚合物，和聚氧化烯聚合物的烷基和芳基醚(例如分子量为1000的甲基-聚异丙二醇醚或分子量为1000-1500的聚乙二醇二苯基醚)；及其单-和多羧酸酯，例如四甘醇的乙酸酯、混合C3-C8脂肪酸酯和C13含氧酸二酯。
硅基油如聚烷基-、聚芳基-、聚烷氧基-或聚芳氧基硅油和硅酸酯油包括另一类有用的合成润滑剂；这种油包括硅酸四乙酯、硅酸四异丙酯、硅酸四-(2-乙基己基)酯、硅酸四-(4-甲基-2-乙基己基)酯、硅酸四-(对-叔丁基-苯基)酯、六-(4-甲基-2-乙基己基)二硅氧烷、聚(甲基)硅氧烷和聚(甲基苯基)硅氧烷。其它合成润滑油包括含磷酸的液体酯(例如磷酸三甲苯酯、磷酸三辛基酯、癸基膦酸的二乙基酯)和聚四氢呋喃。
本发明润滑油组合物任选进一步包含至少一种其它性能添加剂。其它性能添加剂包括分散剂、金属减活剂、清净剂、粘度改进剂、极压剂(通常含硼和/或含硫和/或含磷)、抗磨剂、抗氧化剂(例如受阻酚、胺类抗氧化剂或钼化合物)、腐蚀抑制剂、抑泡剂、反乳化剂、倾点下降剂、密封溶胀剂、摩擦改进剂及其混合物。
存在的其它性能添加剂(不包括粘度改进剂)的总组合量基于无油可包括组合物的0重量％至25重量％，或者0.01重量％至20重量％，或者0.1重量％至15重量％或0.5重量％至10重量％，或者1-5重量％的范围。
尽管可存在一种或多种其它性能添加剂，通常其它性能添加剂以相对于彼此不同的量存在。
在一个实施方案中，润滑组合物进一步包含一种或多种粘度改进剂。
当存在时，粘度改进剂可以以润滑组合物的0.5重量％至70重量％、1重量％至60重量％，或者5重量％至50重量％，或者10重量％至50重量％的量存在。
粘度改进剂包括：(a)聚甲基丙烯酸酯，(b)(i)乙烯基芳族单体和(ii)不饱和羧酸、酐或其衍生物的酯化共聚物，(c)(i)α-烯烃；和(ii)不饱和羧酸、酐或其衍生物的酯化共聚体，或者(d)苯乙烯-丁二烯的氢化共聚物，(e)乙烯-丙烯共聚物，(f)聚异丁烯，(g)氢化苯乙烯-异戊二烯聚合物，(h)氢化异戊二烯聚合物，或者(i)其混合物。
在一个实施方案中，粘度改进剂包括：(a)聚甲基丙烯酸酯，(b)(i)乙烯基芳族单体；和(ii)不饱和羧酸、酐或其衍生物的酯化共聚物，(c)(i)α-烯烃；和(ii)不饱和羧酸、酐或其衍生物的酯化共聚体，或者(d)其混合物。
极压剂包括含有硼和/或硫和/或磷的化合物。
极压剂可以以润滑组合物的0重量％至20重量％，或者0.05重量％至10重量％，或者0.1重量％至8重量％存在于润滑组合物中。
在一个实施方案中，极压剂为含硫化合物。在一个实施方案中，含硫化合物可以为硫化烯烃、多硫化物或其混合物。硫化烯烃的实例包括衍生自丙烯、异丁烯、戊烯的硫化烯烃；有机硫化物和/或多硫化物，包括苄基二硫；双-(氯苄基)二硫；二丁基四硫；二-叔丁基多硫化物；和硫化油酸甲酯、硫化烷基苯酚、硫化二戊烯、硫化萜烯、硫化迪尔斯阿尔德加合物、烷基磺苯基N'N-二烷基二硫代氨基酸酯；或其混合物。
在一个实施方案中，硫化烯烃包括衍生自丙烯、异丁烯、戊烯的硫化烯烃或其混合物。
在一个实施方案中，极压剂含硫化合物包括二巯基噻二唑或者其衍生物或混合物。二巯基噻二唑的实例包括化合物，例如2,5-二巯基-1,3,4-噻二唑或烃基取代2,5-二巯基-1,3,4-噻二唑，或者其低聚物。烃基取代2,5-二巯基-1,3,4-噻二唑的低聚物通常通过在2,5-二巯基-1,3,4-噻二唑单元之间形成硫-硫键以形成具有两个或更多个所述噻二唑单元的衍生物或低聚物而形成。合适的2,5-二巯基-1,3,4-噻二唑衍生化合物包括例如2,5-双(叔壬基二硫代)-1,3,4-噻二唑或2-叔壬基二硫代-5-巯基-1,3,4-噻二唑。烃基取代2,5-二巯基-1,3,4-噻二唑的烃基取代基上的碳原子数目通常包括1-30，或者2-20，或者3-16。
在一个实施方案中，二巯基噻二唑可以为噻二唑-官能化分散剂。关于噻二唑-官能化分散剂的详细描述为国际公开WO 2008/014315的第[0028]至[0052]段。
噻二唑官能化分散剂可通过一种方法制备，所述方法包括将噻二唑化合物与分散剂基质加热、反应或络合。可将噻二唑化合物与分散剂或其混合物共价结合、盐化、络合或者溶解。
用于制备噻二唑官能化分散剂的分散剂基质和噻二唑的相对量可改变。在一个实施方案中，噻二唑化合物相对于100重量份分散剂基质以0.1-10重量份存在。在不同的实施方案中，噻二唑化合物相对于100重量份分散剂基质以大于0.1-9，或者大于0.1至小于5，或者0.2至小于5存在。噻二唑化合物与分散剂基质的相对量也可表示为(0.1-10):100，或者(>0.1-9):100(例如(>0.5-9):100)，或者(0.1至小于5):100，或者(0.2至小于5):100。
在一个实施方案中，分散剂基质相对于1重量份噻二唑化合物以0.1-10重量份存在。在不同的实施方案中，分散剂基质相对于1重量份噻二唑化合物以大于0.1-9，或者大于0.1至小于5，或者约0.2至小于5存在。分散剂基质与噻二唑化合物的相对量也可表示为(0.1-10):1，或者(>0.1-9):1(例如(>0.5-9):1)，或者(0.1至小于5):1，或者(0.2至小于5):1。
噻二唑官能化分散剂可衍生自包含以下分散剂的基质：琥珀酰亚胺分散剂(例如N-取代长链烯基琥珀酰亚胺，通常聚异丁烯琥珀酰亚胺)、曼尼希分散剂、含酯分散剂、脂肪烃基单羧酸酰化剂与胺或氨的缩合产物、烷基氨基苯酚分散剂、烃基胺分散剂、聚醚分散剂、聚醚胺分散剂、包含分散剂功能的粘度改进剂(例如包含分散剂功能的聚合物粘度指数改进剂(VM))或其混合物。在一个实施方案中，分散剂基质包含琥珀酰亚胺分散剂、含酯分散剂或曼尼希分散剂。
在一个实施方案中，极压剂包括含硼化合物。含硼化合物包括硼酸酯(在一些实施方案中，其也可称为硼酸化环氧化物)、硼酸化醇、硼酸化分散剂、硼酸化磷脂或其混合物。在一个实施方案中，含硼化合物可以为硼酸酯或硼酸化醇。
硼酸酯可通过硼化合物和至少一种选自环氧化合物、卤代醇化合物、表卤醇化合物、醇及其混合物化合物反应而制备。醇包括二元醇、三元醇或较高级醇，对于一个实施方案，条件是羟基在相邻碳原子上，即邻近的。
适于制备硼酸酯的硼化合物包括选自硼酸(包括偏硼酸、原硼酸和四硼酸)、氧化硼、三氧化硼和硼酸烷基酯的各种形式。硼酸酯也可由硼卤化物制备。
在一个实施方案中，合适的硼酸酯化合物包括硼酸三丙酯、硼酸三丁酯、硼酸三戊酯、硼酸三己酯、硼酸三庚酯、硼酸三辛酯、硼酸三壬酯和硼酸三癸酯。在一个实施方案中，硼酸酯化合物包括硼酸三丁酯、硼酸三-2-乙基己酯或其混合物。
在一个实施方案中，含硼化合物为通常衍生自N-取代的长链烯基琥珀酰亚胺的硼酸化分散剂。在一个实施方案中，硼酸化分散剂包括聚异丁烯琥珀酰亚胺。硼酸化分散剂更详细地描述于美国专利3,087,936；和专利3,254,025中。
在一个实施方案中，硼酸化分散剂可与含硫化合物或硼酸酯组合使用。
在一个实施方案中，极压剂为不同于硼酸化分散剂的。
衍生出长链烯基的烃的数均分子量包括350-5000，或者500-3000，或者550-1500的范围。长链烯基可具有550或750或950至1000的数均分子量。
将N-取代的长链烯基琥珀酰亚胺使用多种试剂，包括硼酸(例如偏硼酸、原硼酸和四硼酸)、氧化硼、三氧化硼和硼酸烷基酯硼酸化。在一个实施方案中，硼酸化剂为硼酸，其可单独或与其它硼酸化剂组合使用。
硼酸化分散剂可通过将硼酸化合物和N-取代的长链烯基琥珀酰亚胺混合并在合适温度如80-250℃，或90-230℃，或100-210℃下加热它们直至发生所需反应而制备。硼化合物与N-取代的长链烯基琥珀酰亚胺的摩尔比可具有包括10:1-1:4或4:1-1:3在内的范围；或者硼化合物与N-取代的长链烯基琥珀酰亚胺的摩尔比可以为1:2。作为选择，硼酸化分散剂中摩尔B:摩尔N(即B原子:N原子)之比可以为0.25:1-10:1或0.33:1-4:1或0.2:1-1.5:1，或0.25:1-1.3:1或0.8:1-1.2:1或约0.5:1。在进行反应中，可使用惰性液体。该液体可包括甲苯、二甲苯、氯苯、二甲基甲酰胺或其混合物。
在一个实施方案中，润滑组合物进一步包含硼酸化磷脂。硼酸化磷脂可衍生自磷脂的硼酸化(例如硼酸化可用硼酸进行)。磷脂和卵磷脂详细描述于Encyclopedia ofChemical Technology，Kirk和Othmer，第3版，“Fats and Fatty Oils”，第9卷，第795-831页和“Lecithins”，第14卷，第250-269页中。
磷脂可以为任何含有磷酸的类脂，例如卵磷脂或脑磷脂，或其衍生物。磷脂的实例包括磷脂酰胆碱、磷脂酰丝氨酸、磷脂酰肌醇、磷脂酰乙醇胺、磷脂酸及其混合物。磷脂可以为甘油磷脂、上列磷脂的甘油衍生物。通常，甘油磷脂在甘油残基上具有1或2个酰基、烷基或烯基。烷基或烯基可含有8-30，或8-25，或12-24个碳原子。合适的烷基或烯基的实例包括辛基、十二烷基、十六烷基、十八烷基、二十二烷基、辛烯基、十二碳烯基、十六碳烯基和十八碳烯基。
磷脂可合成地制备或衍生自天然来源。合成磷脂可通过本领域技术人员已知的方法制备。天然衍生的磷脂通常通过本领域技术人员已知的程序提取。磷脂可衍生自动物或植物来源。有用的磷脂衍生自葵花籽。磷脂通常含有35-60％磷脂酰胆碱、20-35％磷脂酰肌醇、1-25％磷脂酸和10-25％磷脂酰乙醇胺，其中百分数为基于总磷脂的重量计。脂肪酸含量可以为20-30重量％棕榈酸、2-10重量％硬脂酸、15-25重量％油酸和40-55重量％亚油酸。
摩擦改进剂可包括脂肪胺、酯如硼酸化甘油酯、脂肪亚磷酸酯、脂肪酰胺、脂肪环氧化物、硼酸化脂肪环氧化物、烷氧基化脂肪胺、硼酸化烷氧基化脂肪胺、脂肪酸的金属盐，或脂肪咪唑啉、羧酸和聚亚烷基-多胺的缩合产物。
在一个实施方案中，润滑组合物可含有不同于如上所述描述为磷酸酯胺盐的极压剂的化合物的含磷或含硫抗磨剂。抗磨剂的实例可包括非离子磷化合物(通常具有具有+3或+5氧化态的磷原子的化合物)、金属二烷基二硫代磷酸盐(通常二烷基二硫代磷酸锌)、金属单-或二-烷基磷酸盐(通常磷酸锌)或其混合物。
非离子磷化合物包括亚磷酸酯、磷酸酯或其混合物。
在一个实施方案中，本发明润滑组合物进一步包含分散剂。分散剂可以为琥珀酰亚胺分散剂(如N-取代的长链烯基琥珀酰亚胺)、曼尼希分散剂、含酯分散剂、脂肪烃基单羧酸酰化剂与胺或氨的缩合产物、烷基氨基酚分散剂、烃基胺分散剂、聚醚分散剂或聚醚胺分散剂。
在一个实施方案中，琥珀酰亚胺分散剂包括聚异丁烯-取代的琥珀酰亚胺，其中衍生出分散剂的聚异丁烯可具有400-5000或950-1600的数均分子量。
琥珀酰亚胺分散剂和它们的制备方法更完整地描述于美国专利4,234,435和3,172,892中。
合适的含酯分散剂通常为高分子量酯。这些材料更详细地描述于美国专利3,381,022中。
在一个实施方案中，分散剂包括硼酸化分散剂。通常硼酸化分散剂包括琥珀酰亚胺分散剂，包括聚异丁烯琥珀酰亚胺，其中衍生出分散剂的聚异丁烯可具有400-5000的数均分子量。硼酸化分散剂更详细地描述于以上极压剂的描述内。
分散剂粘度改进剂(通常称为DVM)包括官能化聚烯烃，例如已用马来酸酐和胺的反应产物官能化的乙烯-丙烯共聚物、用胺官能化的聚甲基丙烯酸酯或与胺反应的酯化苯乙烯-马来酸酐共聚物也可用于本发明组合物中。
腐蚀抑制剂包括1-氨基-2-丙醇、辛胺辛酸盐、十二碳烯基琥珀酸或酐和/或脂肪酸如油酸与多胺的缩合产物。
金属减活剂包括苯并三唑(通常为甲苯基三唑)的衍生物、1,2,4-三唑、苯并咪唑、2-烷基二硫代苯并咪唑或2-烷基二硫代苯并噻唑。金属减活剂也可描述为腐蚀抑制剂。
抑泡剂包括丙烯酸乙酯和丙烯酸2-乙基己酯和任选乙酸乙烯酯的共聚物。
反乳化剂包括磷酸三烷基酯，和乙二醇、氧化乙烯、氧化丙烯或其混合物的各种聚合物和共聚物。
倾点下降剂包括马来酸酐-苯乙烯的酯、聚甲基丙烯酸酯、聚丙烯酸酯或聚丙烯酰胺。
密封溶胀剂包括Exxon Necton-37TM(FN 1380)和Exxon Mineral Seal OilTM(FN3200)。
本发明润滑油组合物可用于各种应用，例如轻型、中型和重型发动机油、工业发动机油、船用发动机油、曲轴用油、压缩机油、制冷机用油、烃压缩机油、非常低温润滑油和脂肪、高温润滑油和脂肪、钢缆润滑剂、纺织机油、制冷机油、航空航天润滑剂、航空用涡轮机油、变速器用油、汽轮机油、锭子油、自旋用油、牵引流体、变速器用油、塑料变速器用油、客车变速器用油、货车变速器用油、工业变速器用油、工业齿轮油、绝缘油、仪器用油、刹车流体、变速器流体、缓冲器油、热分布介质油、变压器用油、脂肪、链条用油、用于金属加工操作的最小量润滑剂、用于热和冷加工的油、用于水基金属加工液体的油、用于净油金属加工流体的油、用于半合成金属加工流体的油、用于合成金属加工流体的油、用于土壤勘探的钻井清净剂、液压油、可生物降解润滑剂或润滑油脂或蜡、链锯用油、脱模剂、模制流体、枪、手枪和步枪润滑剂或手表润滑剂和食品级许可润滑剂。
机械装置优选选自轴承、齿轮、接头和导航。优选，机械装置在≥10℃至≤120℃的温度下操作。
实施例
酯化合物的制备
丙基庚醇由BASF SE，Ludwigshafen市购[93.0重量％2-丙基-庚醇；2.9重量％2-丙基-4-甲基-己醇；3.9重量％2-丙基-5-甲基己醇和0.2重量％2-异丙基庚醇]。
DIDA例如作为ES DIDA由BASF SE，Ludwigshafen市购。己二酸二-(2-丙基庚基)酯(DPHA)的制备
使可作为“丙基庚醇”由BASF SE得到的具有10个碳原子的醇的结构异构体(2.4摩尔)和己二酸(1.0摩尔)的混合物在高压釜中在惰性气体(N2)下在230℃的反应温度下在钛酸异丙基-丁酯(0.001摩尔)的存在下反应。在反应期间形成的水通过惰性气流(N2料流)从反应混合物中除去。在180分钟以后，将过量的醇在50毫巴的压力下通过蒸馏从混合物中除去。然后将因此所得的己二酸酯在80℃下用0.5％NaOH中和。其后，将有机相和水相分离，其后将有机相用水洗涤两次。在另一步骤中，通过在180℃和50毫巴下将粗己二酸酯用蒸汽处理而提纯。然后通过使它在150℃和50毫巴下经受N2料流而将酯干燥。最后，将酯与活性炭混合并使用流变剂Supra-Theorit在80℃下在降低的压力下过滤。己二酸酯显示出根据DIN51757，分别地ASTM D 4052测量在20℃下0.916g/cm3的密度。
润滑剂配制剂的制备
表1：润滑剂配制剂A和B(所有值为重量％)
摩擦系数评估
在MTM(微牵引力测定仪)仪器中使用所谓的牵引力试验模式测试流体。以这种模式，摩擦系数以恒定的平均速度经一系列滑滚比(SRR)测量以得到牵引力曲线。SRR＝滑动速度/平均夹带速度＝2(U1-U2)/(U1+U2)，其中U1和U2分别为球和圆盘速度。
用于实验的圆盘和球由钢(AISI 52100)构成，具有750HV的硬度和<0.02μm的Ra。圆盘和球的直径分别为45.0mm和19.0mm。牵引力曲线以1,00GPa接触压力、10-1000m/s速度和不同的温度如40℃和100℃运行。滑滚比(SRR)为50％并测量摩擦系数。各个试样(20ml)运行3次。
评估结果
MTM试验结果显示于图1和2中。每种情况下，上部曲线由配制剂A的评估得到，且下部曲线由配制剂B的评估得到。图1涉及试验在40℃下进行时的结果，而图2涉及试验在100℃下进行时的结果。
每种情况下，包含根据本发明的酯的配制剂显示明显更低的摩擦系数。
Claims (20)
1.在机械装置的润滑中降低润滑油组合物的摩擦系数的方法，其包括：
用可通过使包含以下组分的混合物反应而得到的羧酸酯配制所述润滑油组合物：
a)至少一种二羧酸，任选为其酐的形式，
b1)至少一种具有10个碳原子和通式I结构的单醇：
其中R1为戊基，R2为H且R3为丙基，和
b2)具有10个碳原子和通式II结构的单醇，
其中：
R4选自戊基、2-甲基-丁基、3-甲基-丁基和2,2-二甲基-丙基，
R5为H或甲基，且
R6选自乙基、丙基和异丙基，
其中单醇b1)和单醇b2)具有不同的结构。
2.根据权利要求1的方法，其中摩擦系数在70℃和1GPa下使用微牵引力测定仪(MTM)测量以25％滑滚比(SRR)测量。
3.根据权利要求1的方法，其中二羧酸选自邻苯二甲酸、琥珀酸、烷基琥珀酸、烯基琥珀酸、马来酸、壬二酸、辛二酸、癸二酸、富马酸、己二酸、亚油酸二聚物、丙二酸、烷基丙二酸、烯基丙二酸、戊二酸、二甘醇酸、1,4-环己烷二羧酸、2,6-十氢化萘二羧酸、1,3-环己烷二羧酸和2,5-降莰烷二羧酸。
4.根据权利要求3的方法，其中二羧酸选自戊二酸、二甘醇酸、琥珀酸、壬二酸、癸二酸、1,4-环己烷二羧酸、己二酸、2,6-十氢化萘二羧酸、1,3-环己烷二羧酸和2,5-降莰烷二羧酸。
5.根据权利要求4的方法，其中二羧酸为己二酸。
6.根据权利要求1的方法，其中单醇b1)与单醇b2)的重量比为5:1-95:1。
7.根据权利要求1的方法，其中单醇b1)以相对于酸a)为2.05:1-3.0:1的摩尔比存在。
8.根据权利要求1的方法，其中润滑油组合物包含相对于润滑油组合物的总量≥1％至≤10重量％的至少一种羧酸酯。
9.根据权利要求1的方法，其中润滑油组合物进一步包含选自第I、II或III组矿物油、聚α烯烃、聚合和共聚烯烃、烷基萘、氧化烯聚合物、硅油和磷酸酯的基本油料。
10.根据权利要求9的方法，其中润滑油包含相对于润滑油组合物的总量≥1％至≤49重量％基本油料。
11.根据权利要求1的方法，其中机械装置选自轴承、促动器、齿轮、活塞、曲柄轴、接头和导航。
12.根据权利要求1的方法，其中机械装置在≥10℃至≤120℃的温度下操作。
13.根据权利要求1的方法，其中润滑油组合物包含相对于润滑油组合物的总量≥1％至≤40重量％的至少一种羧酸酯。
14.根据权利要求1的方法，其中润滑油组合物包含相对于润滑油组合物的总量≥20％至≤100重量％的至少一种羧酸酯。
15.根据权利要求9的方法，其中润滑油包含相对于润滑油组合物的总量≥50％至≤99重量％基本油料。
16.根据权利要求1的方法，其中单醇b1)与单醇b2)的重量比为10:1-40:1。
17.根据权利要求1的方法，其中单醇b1)与单醇b2)的重量比为20:1-35:1。
18.在机械装置的润滑中降低润滑油组合物的摩擦系数的方法，其包括：
用通过使包含以下组分的混合物反应而得到的羧酸酯配制所述润滑油组合物：
b)至少一种二羧酸，任选为其酐的形式，
b1)至少一种具有10个碳原子和通式I结构的单醇：
其中R1为戊基，R2为H且R3为丙基，和
b2)具有10个碳原子和通式II结构的单醇，
其中：
R4选自戊基、2-甲基-丁基、3-甲基-丁基和2,2-二甲基-丙基，
R5为H或甲基，且
R6选自乙基、丙基和异丙基，
其中单醇b1)和单醇b2)具有不同的结构，
其中单醇b1)与单醇b2)的重量比为5:1-95:1，
其中单醇b1)以相对于酸a)为2.05:1-3.0:1的摩尔比存在，以及
用所述润滑油组合物润滑机械装置。
19.根据权利要求18的方法，其中机械装置选自轴承、促动器、齿轮、活塞、曲柄轴、接头和导航，机械装置在≥10℃至≤120℃的温度下操作。
20.根据权利要求19的方法，其中单醇b1)与单醇b2)的重量比为20:1-35:1，二羧酸为己二酸。
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2014
- 2014-05-07 HK HK16107728.6A patent/HK1219750A1/zh unknown
- 2014-05-07 PL PL14721890T patent/PL2997117T3/pl unknown
- 2014-05-07 MX MX2015015791A patent/MX2015015791A/es unknown
- 2014-05-07 BR BR112015028363A patent/BR112015028363A2/pt not_active IP Right Cessation
- 2014-05-07 EP EP14721890.3A patent/EP2997117B1/en active Active
- 2014-05-07 US US14/890,741 patent/US9708561B2/en active Active
- 2014-05-07 JP JP2016513290A patent/JP6316406B2/ja active Active
- 2014-05-07 WO PCT/EP2014/059338 patent/WO2014184068A1/en active Application Filing
- 2014-05-07 ES ES14721890T patent/ES2722401T3/es active Active
- 2014-05-07 CN CN201480026817.4A patent/CN105229125B/zh active Active
- 2014-05-07 RU RU2015153251A patent/RU2015153251A/ru not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| PL2997117T3 (pl) | 2019-08-30 |
| EP2997117B1 (en) | 2019-01-30 |
| HK1219750A1 (zh) | 2017-04-13 |
| JP6316406B2 (ja) | 2018-04-25 |
| WO2014184068A1 (en) | 2014-11-20 |
| BR112015028363A2 (pt) | 2017-07-25 |
| CN105229125A (zh) | 2016-01-06 |
| EP2997117A1 (en) | 2016-03-23 |
| JP2016521311A (ja) | 2016-07-21 |
| US20160083667A1 (en) | 2016-03-24 |
| MX2015015791A (es) | 2016-03-15 |
| RU2015153251A (ru) | 2017-06-19 |
| RU2015153251A3 (zh) | 2018-03-21 |
| US9708561B2 (en) | 2017-07-18 |
| ES2722401T3 (es) | 2019-08-09 |
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