JP2013181154A - Grease composition - Google Patents
Grease composition Download PDFInfo
- Publication number
- JP2013181154A JP2013181154A JP2012047664A JP2012047664A JP2013181154A JP 2013181154 A JP2013181154 A JP 2013181154A JP 2012047664 A JP2012047664 A JP 2012047664A JP 2012047664 A JP2012047664 A JP 2012047664A JP 2013181154 A JP2013181154 A JP 2013181154A
- Authority
- JP
- Japan
- Prior art keywords
- amide
- grease composition
- base oil
- solid lubricant
- compound
- 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.)
- Granted
Links
- 239000004519 grease Substances 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- -1 amide compound Chemical class 0.000 claims abstract description 46
- 239000002199 base oil Substances 0.000 claims abstract description 33
- 239000000314 lubricant Substances 0.000 claims abstract description 32
- 229910052751 metal Inorganic materials 0.000 claims abstract description 22
- 239000002184 metal Substances 0.000 claims abstract description 22
- 239000007787 solid Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 21
- 239000000344 soap Substances 0.000 claims abstract description 19
- 239000002562 thickening agent Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 230000001050 lubricating effect Effects 0.000 claims description 16
- 229910000831 Steel Inorganic materials 0.000 abstract description 9
- 239000010959 steel Substances 0.000 abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 150000008431 aliphatic amides Chemical class 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 125000003368 amide group Chemical group 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 229920002545 silicone oil Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 229920013639 polyalphaolefin Polymers 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000008430 aromatic amides Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- FPLIHVCWSXLMPX-UHFFFAOYSA-M lithium 12-hydroxystearate Chemical compound [Li+].CCCCCCC(O)CCCCCCCCCCC([O-])=O FPLIHVCWSXLMPX-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- SWSBIGKFUOXRNJ-CVBJKYQLSA-N ethene;(z)-octadec-9-enamide Chemical compound C=C.CCCCCCCC\C=C/CCCCCCCC(N)=O.CCCCCCCC\C=C/CCCCCCCC(N)=O SWSBIGKFUOXRNJ-CVBJKYQLSA-N 0.000 description 2
- ZJOLCKGSXLIVAA-UHFFFAOYSA-N ethene;octadecanamide Chemical compound C=C.CCCCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCCCC(N)=O ZJOLCKGSXLIVAA-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CPUBMKFFRRFXIP-YPAXQUSRSA-N (9z,33z)-dotetraconta-9,33-dienediamide Chemical compound NC(=O)CCCCCCC\C=C/CCCCCCCCCCCCCCCCCCCCCC\C=C/CCCCCCCC(N)=O CPUBMKFFRRFXIP-YPAXQUSRSA-N 0.000 description 1
- VZGOTNLOZGRSJA-ZZEZOPTASA-N (z)-n-octadecyloctadec-9-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCC\C=C/CCCCCCCC VZGOTNLOZGRSJA-ZZEZOPTASA-N 0.000 description 1
- FYGFTTWEWBXNMP-UHFFFAOYSA-N 10-amino-10-oxodecanoic acid Chemical compound NC(=O)CCCCCCCCC(O)=O FYGFTTWEWBXNMP-UHFFFAOYSA-N 0.000 description 1
- WTHCRRXOPUNKAA-UHFFFAOYSA-N 16-methylheptadecan-1-amine Chemical compound CC(C)CCCCCCCCCCCCCCCN WTHCRRXOPUNKAA-UHFFFAOYSA-N 0.000 description 1
- KZVIUXKOLXVBPC-UHFFFAOYSA-N 16-methylheptadecanamide Chemical compound CC(C)CCCCCCCCCCCCCCC(N)=O KZVIUXKOLXVBPC-UHFFFAOYSA-N 0.000 description 1
- RDYWHMBYTHVOKZ-UHFFFAOYSA-N 18-hydroxyoctadecanamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCO RDYWHMBYTHVOKZ-UHFFFAOYSA-N 0.000 description 1
- XHSVWKJCURCWFU-UHFFFAOYSA-N 19-[3-(19-amino-19-oxononadecyl)phenyl]nonadecanamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCCC1=CC=CC(CCCCCCCCCCCCCCCCCCC(N)=O)=C1 XHSVWKJCURCWFU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DJWFNQUDPJTSAD-UHFFFAOYSA-N n-octadecyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCCCCCCCC DJWFNQUDPJTSAD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MGDIOJPGJAGMGP-UHFFFAOYSA-N pentacosanediamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCCCCCCCC(N)=O MGDIOJPGJAGMGP-UHFFFAOYSA-N 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/06—Mixtures of thickeners and additives
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/065—Sulfides; Selenides; Tellurides
- C10M2201/066—Molybdenum sulfide
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/087—Boron oxides, acids or salts
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/105—Silica
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
- C10M2207/1285—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof used as thickening agents
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- C10M2229/04—Siloxanes with specific structure
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Abstract
Description
本発明は、金属石けん系増ちょう剤を用いるグリース組成物に関する。 The present invention relates to a grease composition using a metal soap thickener.
グリースは、主にすべり軸受けやころがり軸受け（ベアリング）、あるいは接触面が動くために潤滑剤の膜を付着した状態に保つのが難しい摺動面に用いられ、この中でも、金属石けん系増ちょう剤を用いた、いわゆる金属せっけんグリースは、耐水性、耐熱性および機械的安定性に優れ、特に、リチウム石けん系グリースは万能型グリースとして最もよく使用され、鋼と樹脂との摺動部を有する各種軸受、歯車、ボールジョイント、ピニオンなどにも用いられている。 Grease is mainly used for sliding bearings, rolling bearings (bearings), or sliding surfaces where it is difficult to keep the lubricant film attached due to the movement of the contact surface. Among these, metal soap thickeners The so-called metal soap grease using water is excellent in water resistance, heat resistance and mechanical stability, and in particular, lithium soap grease is most commonly used as a universal grease and has various sliding parts between steel and resin. It is also used for bearings, gears, ball joints, pinions and the like.
かかる鋼‐樹脂摺動部で使用される樹脂用グリースとして、シリコーン油及びリチウム石けん増ちょう剤と、ポリテトラフルオロエチレン樹脂粉末を３〜２５質量％、飽和脂肪酸アマイドを１〜１５質量％含有する組成物が提案されている（特許文献１）。
しかし、このグリース組成物は、シリコーン油という密度の大きい基油を用いるため、固体潤滑剤の分散性が悪く、また摩擦係数を十分に下げることができず、スティックスリップも発生し易いという問題があった。
As a grease for resin used in such a steel-resin sliding portion, 3 to 25% by mass of silicone oil and lithium soap thickener, polytetrafluoroethylene resin powder and 1 to 15% by mass of saturated fatty acid amide are contained. A composition has been proposed (Patent Document 1).
However, since this grease composition uses a base oil with a high density called silicone oil, there is a problem that the dispersibility of the solid lubricant is poor, the friction coefficient cannot be lowered sufficiently, and stick slip is likely to occur. there were.
本発明が解決しようとする課題は、固体潤滑剤の分散性を向上させ、鋼と樹脂の摺動部における摩擦係数が十分に低く、スティックスリップの発生がないグリース組成物を提供するものである。 The problem to be solved by the present invention is to provide a grease composition that improves the dispersibility of a solid lubricant, has a sufficiently low coefficient of friction at the sliding portion of steel and resin, and does not cause stick slip. .
本発明者は、かかる課題を解決するために、鋭意、研究を進めた結果、所定の密度を有する潤滑油基油を用いることにより、固体潤滑剤の分散性を高め、鋼と樹脂の摺動部における摩擦係数が十分に低く、スティックスリップの発生がないグリース組成物が得られることを見出した。
本発明は、かかる知見に基づきなされたもので、次のものからなる。
As a result of diligent research, the present inventor has improved the dispersibility of the solid lubricant by using a lubricating base oil having a predetermined density, and the sliding of steel and resin. It was found that a grease composition having a sufficiently low coefficient of friction at the part and no stick-slip was obtained.
This invention is made | formed based on this knowledge, and consists of the following.
（１）１５℃における密度が０.７５〜０.９５g /cm3である潤滑油基油、アミド化合物、固体潤滑剤、及び金属石けん系増ちょう剤を含有するグリース組成物。
（２）固体潤滑剤が、層状化合物またはふっ素樹脂からなる上記（１）に記載されたグリース組成物。
（３）アミド化合物が、モノアミドまたはビスアミドである上記（１）又は（２）に記載されたグリース組成物。
(1) A grease composition containing a lubricating base oil having a density at 15 ° C. of 0.75 to 0.95 g / cm 3 , an amide compound, a solid lubricant, and a metal soap thickener.
(2) The grease composition as described in (1) above, wherein the solid lubricant is a layered compound or a fluororesin.
(3) The grease composition as described in said (1) or (2) whose amide compound is monoamide or bisamide.
本発明のグリース組成物は、固体潤滑剤が十分に分散し、鋼と樹脂の摺動部における摩擦係数が低く、スティックスリップの発生がないという格別の効果を奏する。 The grease composition of the present invention has a special effect that the solid lubricant is sufficiently dispersed, the friction coefficient at the sliding portion of steel and resin is low, and stick slip does not occur.
本発明のグリース組成物は、１５℃における密度が０.７５〜０.９５g /cm3である潤滑油基油、アミド化合物、固体潤滑剤、及び金属石けん系増ちょう剤を含むものである。
〔潤滑油基油〕
本発明の潤滑油基油としては、鉱油系または合成系のいずれも用いることができるが、潤滑油基油の１５℃における密度が、０.７５〜０.９５g/cm3の範囲のものである。この範囲から外れる潤滑油基油では、固体潤滑剤の分散性が低下し、摩擦係数を十分に低くすることはできない。この密度は、特には０.８〜０.９g/cm3のものが好ましい。
また、４０℃における動粘度が１〜５００mm2/sのものが好ましく、５〜１００mm2/sがより好ましい。４０℃における動粘度が１〜５００mm2/sから外れると、所望のちょう度を有するグリース組成物を簡便に調製でき難くなる。さらに、優れた潤滑性を有するグリースを調製するためには、粘度指数が９０以上、特には９５〜２５０、流動点が−１０℃以下、特には−１５〜−７０℃、引火点が１５０℃以上の物性を有する潤滑油基油が好ましい。
The grease composition of the present invention comprises a lubricating base oil having a density at 15 ° C. of 0.75 to 0.95 g / cm 3 , an amide compound, a solid lubricant, and a metal soap thickener.
[Lubricant base oil]
As the lubricating base oil of the present invention, either mineral oil or synthetic oil can be used, but the lubricating base oil has a density at 15 ° C. in the range of 0.75 to 0.95 g / cm 3. is there. When the lubricant base oil is out of this range, the dispersibility of the solid lubricant is lowered, and the friction coefficient cannot be sufficiently lowered. This density is particularly preferably from 0.8 to 0.9 g / cm 3 .
Further, those having a kinematic viscosity at 40 ° C. of 1 to 500 mm 2 / s are preferred, and 5 to 100 mm 2 / s are more preferred. When the kinematic viscosity at 40 ° C. deviates from 1 to 500 mm 2 / s, it becomes difficult to easily prepare a grease composition having a desired consistency. Further, in order to prepare a grease having excellent lubricity, the viscosity index is 90 or more, particularly 95 to 250, the pour point is -10 ° C or less, particularly -15 to -70 ° C, and the flash point is 150 ° C. A lubricating base oil having the above physical properties is preferred.
鉱油系潤滑油基油としては、原油を常圧蒸留し、あるいはさらに減圧蒸留して得られる留出油を各種の精製プロセスで精製した潤滑油留分が挙げられる。精製プロセスは、水素化精製、溶剤抽出、溶剤脱ろう、水素化脱ろう、硫酸洗浄、白土処理などであり、これらを適宜の順序で組み合わせて処理して本発明の基油を得ることができる。異なる原油あるいは留出油を、異なるプロセスの組合せ、順序により得られた、性状の異なる複数の精製油の混合物も有用である。いずれの方法によっても、得られる基油の性状が、前述した密度を満足するように調整することによって好ましく使用することができる。 Examples of the mineral-based lubricating base oil include lubricating oil fractions obtained by purifying distillate obtained by subjecting crude oil to atmospheric distillation or further distillation under reduced pressure by various purification processes. The refining process includes hydrorefining, solvent extraction, solvent dewaxing, hydrodewaxing, sulfuric acid washing, clay treatment, etc., and these can be combined in an appropriate order to obtain the base oil of the present invention. . A mixture of refined oils having different properties, obtained by different crude oils or distillate oils by different process combinations and sequences is also useful. Any method can be preferably used by adjusting the properties of the obtained base oil so as to satisfy the above-described density.
合成系潤滑油基油としては、加水分解安定性に優れる基材を用いることが好ましく、例えばポリ‐α‐オレフィン、ポリブテンや２種以上の各種オレフィンの共重合体などのポリオレフィン、ポリエステル、ポリアルキレングリコール、アルキルベンゼン、アルキルナフタレンなどが挙げられる。なかでも、ポリ‐α‐オレフィンが、入手性、コスト面、粘度特性、酸化安定性、システム部材との適合性の面で好ましい。ポリ‐α‐オレフィンは、１‐ドデセンや１‐デセンなどの重合物がコスト面でさらに好ましい。 As the synthetic lubricant base oil, it is preferable to use a substrate having excellent hydrolysis stability. For example, polyolefins such as poly-α-olefin, polybutene and copolymers of two or more kinds of olefins, polyesters, polyalkylenes Examples thereof include glycol, alkylbenzene, and alkylnaphthalene. Of these, poly-α-olefins are preferable in terms of availability, cost, viscosity characteristics, oxidation stability, and compatibility with system components. The poly-α-olefin is more preferably a polymer such as 1-dodecene or 1-decene in terms of cost.
潤滑油基油は、例示した合成系を単独で、あるいは２種以上混合して用いることができる。さらに、前記鉱油系と混合しても使用することもできる。
合成系潤滑油基油を含めて、複数の潤滑油基油の混合物を使用する場合、該基油混合物が上記物性を満足するものであれば、混合前の個々の基油がかかる物性の範囲を外れていても使用することができる。したがって、個々の合成油系基油は、上記物性を必ずしも満足する必要はないが、上記物性の範囲内であることが好ましい。
この潤滑油基油の含有量は、グリース組成物全量基準で、５０〜９５質量％が好ましく、６０〜８５質量％とすることが特に好ましい。潤滑油基油の含有量が５０〜９５質量％の範囲を外れると所望のちょう度を有するグリース組成物を簡便に調製でき難くなる。
As the lubricating base oil, the exemplified synthetic systems can be used alone or in admixture of two or more. Furthermore, it can also be used by mixing with the mineral oil system.
When using a mixture of a plurality of lubricating base oils including a synthetic base oil, if the base oil mixture satisfies the above physical properties, the individual base oils before mixing are within the range of physical properties. It can be used even if it is off. Accordingly, the individual synthetic base oils do not necessarily satisfy the above physical properties, but are preferably within the above physical properties.
The content of the lubricating base oil is preferably 50 to 95% by mass, particularly preferably 60 to 85% by mass, based on the total amount of the grease composition. When the content of the lubricating base oil is out of the range of 50 to 95% by mass, it becomes difficult to easily prepare a grease composition having a desired consistency.
〔アミド化合物〕
本発明のアミド化合物は、アミド基（‐NH‐CO‐）を少なくとも１つ有する化合物で、アミド化合物として、アミド基を１つ含む化合物（モノアミド）、アミド基を２つ含む化合物（ビスアミド）またはアミド基を３つ含む化合物（トリアミド）のいずれをも用いることができる。ビスアミド、トリアミドは比較的少量でも摺動部の摩擦抵抗を軽減できる利点があり、最も好適である。
モノアミドとしては、モノアミンの酸アミドでも、モノ酸の酸アミドのいずれでも良く、ビスアミドも、ジアミンの酸アミドでも、ジ酸の酸アミドのいずれでも良い。
好ましく用いられるアミド化合物は、融点が４０〜１８０℃、特に好ましくは８０〜１８０℃、更に好ましくは１００〜１７０℃、分子量が２４２〜９３２、特に好ましくは２９８〜８７６のものである。
モノアミド、ビスアミド、及びトリアミドは、下記の一般式（１）、一般式（２）及び（３）、及び一般式（４）でそれぞれ表される。
[Amide compound]
The amide compound of the present invention is a compound having at least one amide group (-NH-CO-). As the amide compound, a compound containing one amide group (monoamide), a compound containing two amide groups (bisamide) or Any compound (triamide) containing three amide groups can be used. Bisamide and triamide are most preferred because they have the advantage of reducing the frictional resistance of the sliding portion even with a relatively small amount.
The monoamide may be either a monoamine acid amide or a monoacid acid amide, and may be a bisamide, a diamine acid amide, or a diacid acid amide.
The amide compound preferably used is one having a melting point of 40 to 180 ° C., particularly preferably 80 to 180 ° C., more preferably 100 to 170 ° C., and a molecular weight of 242 to 932, particularly preferably 298 to 876.
Monoamide, bisamide, and triamide are represented by the following general formula (1), general formula (2) and (3), and general formula (4), respectively.
R1‐CO‐NH‐R2 ・・・・（１）
R1‐CO‐NH‐A1‐NH‐CO‐R2 ・・・・（２）
R1‐NH‐CO‐A1‐CO‐NH‐R2 ・・・・（３）
R1‐M‐A1‐CH（A2‐M‐R3）‐A3‐M‐R2・・・・（４）
R 1 -CO-NH-R 2 (1)
R 1 -CO-NH-A 1 -NH-CO-R 2 (2)
R 1 -NH-CO-A 1 -CO-NH-R 2 (3)
R 1 -M-A 1 -CH (A 2 -M-R 3 ) -A 3 -M-R 2 (4)
上記各式において、R1、R2、R3は、それぞれ独立して、炭素数５〜２５の炭化水素基で、脂肪族炭化水素基、脂環族炭化水素基または芳香族炭化水素基のいずれでもよい。また、一般式（１）の場合にはR2が水素の場合も含む。A1、A2、A3は、それぞれ独立して、炭素数１〜１０の脂肪族炭化水素基、脂環族炭化水素基又は芳香族炭化水素基、またはこれらが組み合わされたかたちの炭素数１〜１０の２価の炭化水素基で、Ｍはアミド基である。
なお、モノアミドの場合、R2が水素又は炭素数１０〜２０の飽和又は不飽和の鎖状炭化水素基であることが好ましい。
また、ジアミンの酸アミドの場合は、A1が炭素数１〜４の２価の飽和鎖状炭化水素基のものが好ましい。
さらに、式（２）及び（３）において、R1、R2、またはA1で表される炭化水素基は、一部の水素が水酸基（‐OH）で置換されていてもよい。
In each of the above formulas, R 1 , R 2 and R 3 are each independently a hydrocarbon group having 5 to 25 carbon atoms, which is an aliphatic hydrocarbon group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group. Either is acceptable. In the case of the general formula (1), the case where R 2 is hydrogen is also included. A 1 , A 2 , and A 3 are each independently an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a combination of these carbon numbers 1-10 divalent hydrocarbon groups, M is an amide group.
In the case of monoamide, R 2 is preferably hydrogen or a saturated or unsaturated chain hydrocarbon group having 10 to 20 carbon atoms.
In the case of a diamine acid amide, A 1 is preferably a divalent saturated chain hydrocarbon group having 1 to 4 carbon atoms.
Furthermore, in the formulas (2) and (3), in the hydrocarbon group represented by R 1 , R 2 , or A 1 , a part of hydrogen may be substituted with a hydroxyl group (—OH).
本明細書においては、A1、A2およびA3が脂肪族炭化水素基であるアミド化合物を脂肪族アミドと、A1、A2またはA3の少なくとも一つが芳香族炭化水素基であるアミド化合物を芳香族アミドと、また、A1、A2またはA3の少なくとも一つが脂環族炭化水素基または芳香族炭化水素基であるアミド化合物を非脂肪族アミドという。
脂肪族アミドの場合、R1、R2、R3は炭素数１０〜２０の飽和又は不飽和の鎖状炭化水素基であることが好ましい。
芳香族アミドの場合、R1、R2、R3は炭素数１０〜２０の飽和又は不飽和の鎖状炭化水素基と芳香族炭化水素基のものが好ましい。
アミド化合物としては、非脂肪族アミドを用いることができるが、脂肪族アミドが好ましい。ジアミンの酸アミド（一般式（３））の場合は、A1が炭素数１〜４の２価の飽和鎖状炭化水素基のものが好ましい。
In the present specification, an amide compound in which A 1 , A 2 and A 3 are aliphatic hydrocarbon groups is an aliphatic amide, and an amide in which at least one of A 1 , A 2 or A 3 is an aromatic hydrocarbon group The compound is referred to as an aromatic amide, and the amide compound in which at least one of A 1 , A 2, or A 3 is an alicyclic hydrocarbon group or an aromatic hydrocarbon group is referred to as a non-aliphatic amide.
In the case of an aliphatic amide, R 1 , R 2 and R 3 are preferably a saturated or unsaturated chain hydrocarbon group having 10 to 20 carbon atoms.
In the case of an aromatic amide, R 1 , R 2 , and R 3 are preferably those having a saturated or unsaturated chain hydrocarbon group having 10 to 20 carbon atoms and an aromatic hydrocarbon group.
As the amide compound, a non-aliphatic amide can be used, but an aliphatic amide is preferred. In the case of a diamine acid amide (general formula (3)), A 1 is preferably a divalent saturated chain hydrocarbon group having 1 to 4 carbon atoms.
モノアミドとしては、具体的には、ラウリン酸アミド、パルミチン酸アミド、ステアリン酸アミド、ベヘン酸アミド、ヒドロキシステアリン酸アミド等の飽和脂肪酸アミド、オレイン酸アミド、エルカ酸アミドなどの不飽和脂肪酸アミド、及びステアリルステアリン酸アミド、オレイルオレイン酸アミド、オレイルステアリン酸アミド、ステアリルオレイン酸アミド等の飽和又は不飽和の長鎖脂肪酸と長鎖アミンによる置換アミド類などが挙げられる。 Specific examples of monoamides include saturated fatty acid amides such as lauric acid amide, palmitic acid amide, stearic acid amide, behenic acid amide, hydroxystearic acid amide, unsaturated fatty acid amides such as oleic acid amide and erucic acid amide, and Examples thereof include substituted amides of saturated or unsaturated long-chain fatty acids and long-chain amines such as stearyl stearamide, oleyl oleate amide, oleyl stearate amide, stearyl oleamide.
式（２）で表されるジアミンの酸アミドとしては、具体的には、エチレンビスステアリン酸アミド、エチレンビスイソステアリン酸アミド、エチレンビスオレイン酸アミド、メチレンビスラウリン酸アミド、ヘキサメチレンビスオレイン酸アミド、ヘキサメチレンビスヒドロキシステアリン酸アミド等が挙げられる。式（３）で表されるジ酸のビスアミドとしては、具体的には、Ｎ,Ｎ'‐ビスステアリルセバシン酸アミド等が挙げられる。
これらビスアミドの中でも、式（２）及び式（３）のR1とR2がそれぞれ独立して炭素数１２〜２０の飽和鎖状炭化水素基又は不飽和鎖状炭化水素基のアミド化合物であることが好ましい。
Specific examples of the acid amide of the diamine represented by the formula (2) include ethylene bis stearic acid amide, ethylene bis isostearic acid amide, ethylene bis oleic acid amide, methylene bis lauric acid amide, and hexamethylene bis oleic acid amide. And hexamethylene bishydroxystearic acid amide. Specific examples of the diacid bisamide represented by the formula (3) include N, N′-bisstearyl sebacic acid amide.
Among these bisamides, R 1 and R 2 in formula (2) and formula (3) are each independently an amide compound having a saturated chain hydrocarbon group or unsaturated chain hydrocarbon group having 12 to 20 carbon atoms. It is preferable.
一般式（４）で表されるトリアミドは多数あるが、本発明に好適に用いることができる化合物として具体的にはＮ‐アシルアミノ酸ジアミド化合物が挙げられる。この化合物のＮ‐アシル基は、炭素数１〜３０の直鎖又は分枝の飽和又は不飽和の脂肪族アシル基又は芳香族アシル基、特にはカプロイル基、カプリロイル基、ラウロイル基、ミリストイル基、ステアロイル基からなるものが好ましく、またアミノ酸としてはアスパラギン酸、グルタミン酸からなるものが好ましく、また、アミド基のアミンは炭素数１〜３０の直鎖又は分枝の飽和又は不飽和の脂肪族アミン、特にはブチルアミン、オクチルアミン、ラウリルアミン、イソステアリルアミン、ステアリルアミン等が好ましい。特には、具体的な化合物としてＮ‐ラウロイル‐Ｌ‐グルタミン酸‐α,γ‐ジ‐ｎ‐ブチルアミドが好ましい。 There are many triamides represented by the general formula (4), and specific examples of compounds that can be suitably used in the present invention include N-acylamino acid diamide compounds. The N-acyl group of this compound is a linear or branched saturated or unsaturated aliphatic acyl group or aromatic acyl group having 1 to 30 carbon atoms, particularly a caproyl group, capryloyl group, lauroyl group, myristoyl group, Those composed of stearoyl groups are preferred, and as amino acids are preferably composed of aspartic acid and glutamic acid, and the amine of the amide group is a linear or branched saturated or unsaturated aliphatic amine having 1 to 30 carbon atoms, In particular, butylamine, octylamine, laurylamine, isostearylamine, stearylamine and the like are preferable. In particular, N-lauroyl-L-glutamic acid-α, γ-di-n-butyramide is preferred as a specific compound.
上記アミド化合物はそれぞれ単独で用いても、２種以上の割合で組み合わせて用いてもよい。このアミド化合物の含有量は、グリース組成物全量基準で、１〜５０質量％とすることが好ましく、５〜３０質量％が好ましい。
なお、このアミド化合物は潤滑油基油の存在下で加熱溶融すると、三次元網目構造を形成するアミド化合物中に潤滑油基油が保持された状態になり、ただ単にアミド化合物をグリース中に分散、混合した場合に比べて、鋼と樹脂の摺動部における摩擦係数がさらに低くなり、またスティックスリップの発生が全く生じない。
The amide compounds may be used alone or in combination of two or more. The content of the amide compound is preferably 1 to 50% by mass and more preferably 5 to 30% by mass based on the total amount of the grease composition.
When this amide compound is heated and melted in the presence of a lubricant base oil, the lubricant base oil is held in the amide compound forming a three-dimensional network structure, and the amide compound is simply dispersed in the grease. Compared to the case of mixing, the friction coefficient at the sliding portion of steel and resin is further reduced, and no stick slip occurs.
〔固体潤滑剤〕
固体潤滑剤は、一般に潤滑剤に使用されているものであれば特に限定されないが、潤滑性が優れている層状化合物またはふっ素樹脂を用いることが好ましい。
層状化合物としては、層状の結晶構造を有するもので、例えば、メラミンシアヌレート、二硫化モリブデン、窒化ホウ素、黒鉛、雲母、フッ化黒鉛などが好適である。
ふっ素樹脂としては、ポリテトラフルオロエチレン（ＰＴＦＥ）、テトラフルオロエチレン・パーフルオロアルキルビニルエーテル共重合体（ＰＦＡ）、テトラフルオロエチレン・ヘキサフルオロプロピレン共重合体（ＦＥＰ）、テトラフルオロエチレン・エチレン共重合体（ＥＴＦＥ）、ポリビニリデンフルオライド（ＰＶＤＦ）、ポリクロロトリフルオロエチレン（ＰＣＴＦＥ）等などが好適である。
これらの固体潤滑剤は単独又は２種以上混合して用いることができ、また、使用用途により適正な粒径のものを適宜選定して使用できるが、粒子直径が０.２〜５０μｍ、特には１〜１０μｍのものが好ましい。
この固体潤滑剤の含有量は、グリース組成物の全量基準で、０.１〜１０質量％、特には０.２〜５質量％とすることが好ましい。
[Solid lubricant]
The solid lubricant is not particularly limited as long as it is generally used for a lubricant, but it is preferable to use a layered compound or a fluorine resin having excellent lubricity.
As the layered compound, those having a layered crystal structure, for example, melamine cyanurate, molybdenum disulfide, boron nitride, graphite, mica, fluorinated graphite and the like are suitable.
Examples of fluororesins include polytetrafluoroethylene (PTFE), tetrafluoroethylene / perfluoroalkyl vinyl ether copolymer (PFA), tetrafluoroethylene / hexafluoropropylene copolymer (FEP), and tetrafluoroethylene / ethylene copolymer. (ETFE), polyvinylidene fluoride (PVDF), polychlorotrifluoroethylene (PCTFE) and the like are suitable.
These solid lubricants can be used alone or as a mixture of two or more thereof, and those having an appropriate particle size can be appropriately selected and used depending on the intended use, but the particle diameter is 0.2 to 50 μm, particularly The thing of 1-10 micrometers is preferable.
The content of the solid lubricant is preferably 0.1 to 10% by mass, particularly 0.2 to 5% by mass, based on the total amount of the grease composition.
〔金属石けん系増ちょう剤〕
金属石けん系増ちょう剤は、カルボン酸金属塩からなる増ちょう剤であり、カルボン酸はヒドロキシ基などを有するカルボン酸誘導体であってもよい。
カルボン酸は、ステアリン酸、アゼライン酸などの脂肪族カルボン酸でも、テレフタル酸などの芳香族カルボン酸でもよいが、１価または２価の脂肪族カルボン酸、特には炭素数６〜２０の脂肪族カルボン酸が用いられる。特には、炭素数１２〜２０の１価脂肪族カルボン酸や炭素数６〜１４の２価脂肪族カルボン酸が好ましく用いられる。１個のヒドロキシル基を含む１価脂肪族カルボン酸が好ましい。
金属としては、リチウム、ナトリウムなどのアルカリ金属、カルシウムなどのアルカリ土類金属、アルミニウムのような両性金属でもよいが、アルカリ金属、特にはリチウムが好ましく用いられる。
[Metal soap thickener]
The metal soap-based thickener is a thickener made of a carboxylic acid metal salt, and the carboxylic acid may be a carboxylic acid derivative having a hydroxy group or the like.
The carboxylic acid may be an aliphatic carboxylic acid such as stearic acid or azelaic acid, or an aromatic carboxylic acid such as terephthalic acid, but a monovalent or divalent aliphatic carboxylic acid, particularly an aliphatic group having 6 to 20 carbon atoms. Carboxylic acid is used. In particular, monovalent aliphatic carboxylic acids having 12 to 20 carbon atoms and divalent aliphatic carboxylic acids having 6 to 14 carbon atoms are preferably used. Monovalent aliphatic carboxylic acids containing one hydroxyl group are preferred.
The metal may be an alkali metal such as lithium or sodium, an alkaline earth metal such as calcium, or an amphoteric metal such as aluminum, but an alkali metal, particularly lithium, is preferably used.
なお、この増ちょう剤は、金属石けんの形で配合してもよいが、カルボン酸と金属源（金属塩、金属塩水酸化物等）を別々に配合して、グリース作製時に反応させて、金属石けん増ちょう剤としてもよい。
このようなカルボン酸金属塩は、一種類でも複数の種類を混合して用いてもよい。例えば、１２‐ヒドロキシステアリン酸リチウムとアゼライン酸リチウムの混合物は特に好ましい。
金属石けん系増ちょう剤の含有量は、所望のちょう度が得られれば良く、例えば、グリース組成物の全量基準で、好ましくは２〜３０質量％、さらに好ましくは５〜１５％である。
This thickener may be blended in the form of metal soap, but a carboxylic acid and a metal source (metal salt, metal salt hydroxide, etc.) are blended separately and reacted at the time of grease preparation, It may be a soap thickener.
Such carboxylic acid metal salts may be used singly or in combination. For example, a mixture of lithium 12-hydroxystearate and lithium azelate is particularly preferred.
The content of the metal soap thickener may be a desired consistency, and is, for example, preferably 2 to 30% by mass, more preferably 5 to 15%, based on the total amount of the grease composition.
〔その他の添加剤〕
本発明のグリース組成物には、上記成分以外に、必要に応じて、一般に潤滑油やグリースに用いられている、清浄剤、分散剤、摩耗防止剤、粘度指数向上剤、酸化防止剤、極圧剤、防錆剤、腐食防止剤などを適宜添加することができる。
[Other additives]
In addition to the above components, the grease composition of the present invention includes, as necessary, a detergent, a dispersant, an antiwear agent, a viscosity index improver, an antioxidant, an electrode, which are generally used in lubricating oils and greases. A pressure agent, a rust inhibitor, a corrosion inhibitor, and the like can be added as appropriate.
〔調製方法〕
本発明のグリース組成物は、一般的なグリースの製造方法で作製できるが、アミド化合物を混合後に、その融点以上に一度加熱することが好ましい。
すなわち、アミド化合物と潤滑油基油をアミド化合物の融点以上に加熱して冷却後、固体潤滑剤と増ちょう剤と潤滑油基油からなる一般的なグリースと物理的に混合する方法でもよく、また、増ちょう剤を含む全ての成分を混合した後に、アミド化合物の融点以上に加熱して冷却することでもよい。
[Preparation method]
The grease composition of the present invention can be produced by a general method for producing grease, but it is preferable to heat the amide compound once after its melting point after mixing.
In other words, the amide compound and the lubricating base oil may be heated to the melting point of the amide compound or higher and cooled, and then physically mixed with a general grease composed of a solid lubricant, a thickener, and a lubricating base oil. Moreover, after mixing all the components containing a thickener, it may be heated to the melting point or higher of the amide compound and cooled.
〔潤滑対象〕
本発明のグリース組成物は、種々の樹脂製摺動部材と金属製摺動部材の潤滑に好適に用いられる。例えば、樹脂製摺動部材として、UL規格の長期耐熱温度が５０〜１５０℃を有する、ナイロン樹脂、ポリカーボネート（PC）樹脂、ポリブチレンテレフタレート（PBT）樹脂、ポリアセタール（POM）樹脂などであり、特にナイロンPA6樹脂が用いられている部材に好適で、また、金属製摺動部材として、軸受鋼、炭素鋼、ステンレス鋼（SUS）などであり、特に、軸受鋼SUJ‐2が用いられている部材に好適である。
[Lubrication target]
The grease composition of the present invention is suitably used for lubrication of various resin sliding members and metal sliding members. Examples of resin sliding members include nylon resin, polycarbonate (PC) resin, polybutylene terephthalate (PBT) resin, polyacetal (POM) resin, etc., which have a UL standard long-term heat-resistant temperature of 50 to 150 ° C. Suitable for members using nylon PA6 resin, and as metal sliding members, bearing steel, carbon steel, stainless steel (SUS), etc., especially members using bearing steel SUJ-2 It is suitable for.
１．潤滑油基油
（１）鉱油系潤滑油基油
・常圧蒸留残渣を減圧蒸留して得られた留出油を溶剤精製した潤滑油基油
４０℃における動粘度；６８mm2/s
１５℃における密度；０.８７g/cm3
粘度指数；１００
流動点；−１０℃
引火点；２５０℃
1. Lubricant base oil (1) Mineral oil base oil / Lubricant base oil obtained by solvent-refining distillate obtained by distillation under reduced pressure from atmospheric distillation residue Kinematic viscosity at 40 ° C; 68 mm 2 / s
Density at 15 ° C; 0.87 g / cm 3
Viscosity index: 100
Pour point: -10 ° C
Flash point: 250 ° C
（２）合成系潤滑油基油
（ａ）ポリαオレフィン（INEOS社製Durasyn170）
４０℃における動粘度；６８mm2/s
１５℃における密度：０.８３g/cm3
粘度指数；１３３
流動点；−４５℃
引火点；２５０℃
（ｂ）ポリジメチルシロキサン（シリコーン油；信越化学社製KF‐96 50cs,100cs）
４０℃における動粘度；６８mm2/s
１５℃における密度：０.９６g/cm3
（ｃ）直鎖型パーフルオロポリエーテル（フッ化油；ソルベイソレクシス社製FOMBLIN M15）
４０℃における動粘度；８５mm2/s
１５℃における密度：１.８３g/cm3
(2) Synthetic lubricating base oil (a) Poly-alpha olefin (Durasyn 170 manufactured by INEOS)
Kinematic viscosity at 40 ° C; 68 mm 2 / s
Density at 15 ° C .: 0.83 g / cm 3
Viscosity index; 133
Pour point: -45 ° C
Flash point: 250 ° C
(B) Polydimethylsiloxane (silicone oil; KF-96 50cs, 100cs manufactured by Shin-Etsu Chemical Co., Ltd.)
Kinematic viscosity at 40 ° C; 68 mm 2 / s
Density at 15 ° C .: 0.96 g / cm 3
(C) Linear perfluoropolyether (fluorinated oil; FOMBLIN M15 manufactured by Solvay Solexis)
Kinematic viscosity at 40 ° C; 85 mm 2 / s
Density at 15 ° C .: 1.83 g / cm 3
２．アミド化合物
（１）脂肪族アミド
（ａ）エチレンビスステアリン酸アミド（特級試薬）
（ｂ）エチレンビスオレイン酸アミド（特級試薬）
（ｃ）ステアリン酸モノアミド（特級試薬）
（２）芳香族アミド
（ａ）ｍ‐キシリレンビスステアリン酸アミド（特級試薬）
2. Amide compound (1) Aliphatic amide (a) Ethylene bis-stearic acid amide (special grade reagent)
(B) Ethylene bisoleic acid amide (special grade reagent)
(C) Stearic acid monoamide (special grade reagent)
(2) Aromatic amide (a) m-xylylene bis-stearic acid amide (special grade reagent)
３．固体潤滑剤
（１）メラミンシアヌレート（ＭＣＡ、平均粒径；４μm、BASF社製MELAPUR MC25）
（２）二硫化モリブデン（平均粒径；０.５μm、ダイゾーニチモリ社製ニチモリM‐5パウダー）
（３）ポリテトラフルオロエチレン（ＰＴＦＥ、平均粒子径；４μm、喜多村社製KTL‐8N）
（４）窒化ホウ素（平均粒子径；２μm、水島合金鉄社製HP‐P1）
（５）酸化ケイ素（平均粒子径；３５μm、特級試薬）
なお、平均粒子径は、レーザー光回折法により測定したものである。
3. Solid lubricant (1) Melamine cyanurate (MCA, average particle diameter: 4 μm, MELAPUR MC25 manufactured by BASF)
(2) Molybdenum disulfide (average particle size: 0.5 μm, Nichimori M-5 powder manufactured by Daizonitori)
(3) Polytetrafluoroethylene (PTFE, average particle size: 4 μm, KTL-8N manufactured by Kitamura)
(4) Boron nitride (average particle size: 2 μm, HP-P1 manufactured by Mizushima Alloy Iron Company)
(5) Silicon oxide (average particle size: 35 μm, special grade reagent)
The average particle diameter is measured by a laser light diffraction method.
４．金属石けん系増ちょう剤
（１）１２‐ヒドロキシステアリン酸リチウム（表では「ステアリン酸リチウム」と表記）
（２）１２‐ヒドロキシステアリン酸リチウムとアゼライン酸リチウムの複合体（混合割合は２：１）（表では「複合リチウム石けん」と表記）
５．他の添加剤
酸化防止剤としてジフェニルアミンを全てに添加した。
4). Metal soap thickener (1) Lithium 12-hydroxystearate (shown as “lithium stearate” in the table)
(2) Composite of lithium 12-hydroxystearate and lithium azelate (mixing ratio is 2: 1) (shown as “composite lithium soap” in the table)
5. Other additives Diphenylamine was added to all as an antioxidant.
〔調製方法〕
各成分を表１、表２に示す配合量（質量％で示す）で容器に入れ、１５０℃（アミドの融点以上）に加熱して、マグネチックスターラーで攪拌したのち、室温に冷却した。これをローラ（３本ロール）で加圧分散処理を行い、グリース組成物を調製した。
[Preparation method]
Each component was placed in a container at the blending amounts (shown in mass%) shown in Tables 1 and 2, heated to 150 ° C. (above the melting point of the amide), stirred with a magnetic stirrer, and then cooled to room temperature. This was subjected to pressure dispersion treatment with a roller (three rolls) to prepare a grease composition.
〔評価方法〕
ボールとディスクの往復動摩擦試験機で評価試験を行った。金属摺動部材として、SUJ‐2の直径１/４インチ球及び樹脂製摺動部材として６ナイロンのプレート状のもの〔東洋プラスチック精工社製N6（NC）〕を用いた。
試験荷重は２０００gf、摺動速度は１０mm/s、振幅２０mmとし、ディスクにグリースを塗布し、摺動させたときの摩擦係数と摩擦力の波形からスティックスリップの発生の有無を評価した（一方向に摺動中の摩擦力が一定でない場合にスティックスリップが発生しているとした）。
〔Evaluation method〕
An evaluation test was conducted with a ball-disk reciprocating friction tester. As the metal sliding member, a 1/4 inch sphere of SUJ-2 diameter and a 6 nylon plate-like member (N6 (NC) manufactured by Toyo Plastic Seiko Co., Ltd.) as a resin sliding member were used.
The test load was 2000 gf, the sliding speed was 10 mm / s, and the amplitude was 20 mm. Grease was applied to the disk, and the presence or absence of stick-slip was evaluated from the friction coefficient and the frictional force waveform when slid. In addition, stick slip occurs when the frictional force during sliding is not constant).
〔評価結果〕
鉱油とリチウム石けん系増ちょう剤のみを配合した場合、摩擦係数が高く、スティックスリップの発生も確認された（比較例７）。
鉱油とリチウム石けん系増ちょう剤と固体潤滑剤のみを配合した場合、摩擦係数が僅かに低減、スティックスリップも若干低減されたが十分ではなかった（比較例１−６）。
鉱油とリチウム石けんと固体潤滑剤と脂肪族アミドを配合した場合、摩擦係数がさらに低減し、スティックスリップの発生も抑制された（実施例１−１２）。
基油にシリコーン油やフッ化油を用いた場合、アミド化合物の融点以上に加熱しても、融解したアミド化合物と基油が２相に分離し、均一に溶解しなかった（比較例８、９）。そのためシリコーン油には酸化ケイ素を、フッ化油にはポリテトラフルオロエチレンを添加したが、不均一な仕上がりとなったため、摩擦試験は実施できなかった（比較例１０、１１）。
〔Evaluation results〕
When only mineral oil and a lithium soap thickener were blended, the friction coefficient was high and the occurrence of stick-slip was also confirmed (Comparative Example 7).
When only mineral oil, a lithium soap thickener and a solid lubricant were blended, the friction coefficient was slightly reduced and stick slip was slightly reduced, but it was not sufficient (Comparative Example 1-6).
When mineral oil, lithium soap, solid lubricant, and aliphatic amide were blended, the friction coefficient was further reduced, and the occurrence of stick slip was also suppressed (Example 1-12).
When silicone oil or fluorinated oil was used as the base oil, the melted amide compound and the base oil separated into two phases even when heated to a temperature higher than the melting point of the amide compound, and did not dissolve uniformly (Comparative Example 8, 9). For this reason, silicon oxide was added to the silicone oil and polytetrafluoroethylene was added to the fluorinated oil, but the friction test could not be carried out because of non-uniform finish (Comparative Examples 10 and 11).
本発明のグリース組成物は、固体潤滑剤が十分に分散し、鋼と樹脂の摺動部における摩擦係数が低く、スティックスリップの発生がないので、樹脂製摺動部材と金属製摺動部材、例えば、各種軸受、歯車、ボールジョイント、ピニオンなどの潤滑に有用である。 In the grease composition of the present invention, the solid lubricant is sufficiently dispersed, the coefficient of friction in the sliding portion of steel and resin is low, and there is no occurrence of stick-slip. For example, it is useful for lubricating various bearings, gears, ball joints, pinions and the like.
Claims (3)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012047664A JP5931509B2 (en) | 2012-03-05 | 2012-03-05 | Grease composition |
| EP13757011.5A EP2824166B1 (en) | 2012-03-05 | 2013-03-01 | Grease composition |
| US14/382,846 US20150024980A1 (en) | 2012-03-05 | 2013-03-01 | Grease composition |
| CN201380012539.2A CN104145011A (en) | 2012-03-05 | 2013-03-01 | Grease composition |
| KR1020147027506A KR102051689B1 (en) | 2012-03-05 | 2013-03-01 | Grease composition |
| SG11201404820RA SG11201404820RA (en) | 2012-03-05 | 2013-03-01 | Grease composition |
| PCT/JP2013/055623 WO2013133148A1 (en) | 2012-03-05 | 2013-03-01 | Grease composition |
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| JP2012047664A JP5931509B2 (en) | 2012-03-05 | 2012-03-05 | Grease composition |
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| JP2013181154A true JP2013181154A (en) | 2013-09-12 |
| JP5931509B2 JP5931509B2 (en) | 2016-06-08 |
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| US (1) | US20150024980A1 (en) |
| EP (1) | EP2824166B1 (en) |
| JP (1) | JP5931509B2 (en) |
| KR (1) | KR102051689B1 (en) |
| CN (1) | CN104145011A (en) |
| SG (1) | SG11201404820RA (en) |
| WO (1) | WO2013133148A1 (en) |
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| WO2016143807A1 (en) * | 2015-03-09 | 2016-09-15 | Ｊｘエネルギー株式会社 | Grease composition |
| JP2017149905A (en) * | 2016-02-26 | 2017-08-31 | 協同油脂株式会社 | Grease composition for ball joint |
| WO2019151332A1 (en) * | 2018-01-31 | 2019-08-08 | 出光興産株式会社 | Grease composition |
| CN116218582A (en) * | 2023-01-05 | 2023-06-06 | 中国石油化工股份有限公司 | Worm gear lubricating grease composition for EPS steering gear of automobile and application thereof |
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| JP6454541B2 (en) * | 2014-12-25 | 2019-01-16 | 株式会社日立製作所 | Lubricant for gas insulated switchgear and gas insulated switchgear |
| JP6753699B2 (en) * | 2016-05-27 | 2020-09-09 | ミネベアミツミ株式会社 | Rolling bearing |
| WO2019133255A1 (en) | 2017-12-29 | 2019-07-04 | Exxonmobil Research And Engineering Company | Grease compositions with improved performance comprising thixotropic polyamide, and methods of preparing and using the same |
| TW202021811A (en) * | 2018-12-14 | 2020-06-16 | 美商陶氏全球科技有限責任公司 | Multilayer films and laminates containing slip agents |
| AU2022397936A1 (en) * | 2021-11-24 | 2024-05-09 | Klueber Lubrication Muenchen Gmbh & Co. Kg | High-temperature grease |
| EP4186966A1 (en) * | 2021-11-24 | 2023-05-31 | Klüber Lubrication München SE & Co. KG | High temperature lubricant grease |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2824166A1 (en) | 2015-01-14 |
| CN104145011A (en) | 2014-11-12 |
| KR102051689B1 (en) | 2019-12-03 |
| EP2824166A4 (en) | 2015-11-04 |
| SG11201404820RA (en) | 2014-11-27 |
| EP2824166B1 (en) | 2020-05-06 |
| JP5931509B2 (en) | 2016-06-08 |
| KR20140129351A (en) | 2014-11-06 |
| US20150024980A1 (en) | 2015-01-22 |
| WO2013133148A1 (en) | 2013-09-12 |
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