JP2010528156A5 - - Google Patents
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- JP2010528156A5 JP2010528156A5 JP2010509454A JP2010509454A JP2010528156A5 JP 2010528156 A5 JP2010528156 A5 JP 2010528156A5 JP 2010509454 A JP2010509454 A JP 2010509454A JP 2010509454 A JP2010509454 A JP 2010509454A JP 2010528156 A5 JP2010528156 A5 JP 2010528156A5
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- 239000000203 mixture Substances 0.000 claims description 49
- 230000001050 lubricating Effects 0.000 claims description 48
- -1 ester amide Chemical class 0.000 claims description 19
- 239000005078 molybdenum compound Substances 0.000 claims description 17
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 13
- 229910052750 molybdenum Inorganic materials 0.000 claims description 12
- 239000011733 molybdenum Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 8
- 238000002485 combustion reaction Methods 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- KHYKFSXXGRUKRE-UHFFFAOYSA-J C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S 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 claims description 5
- 230000003078 antioxidant Effects 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 4
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl N-hexyl-N-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 229960001367 tartaric acid Drugs 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N Diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N Succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910000071 diazene Inorganic materials 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 150000003873 salicylate salts Chemical class 0.000 claims description 2
- 229960002317 succinimide Drugs 0.000 claims description 2
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical class [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 claims description 2
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 description 4
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- JJULABXIXFRDCQ-UHFFFAOYSA-N 2,3,4-tritert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C JJULABXIXFRDCQ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N Octadecene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 231100000693 bioaccumulation Toxicity 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000003892 tartrate salts Chemical class 0.000 description 2
- OBDUMNZXAIUUTH-HWKANZROSA-N (E)-tetradec-2-ene Chemical compound CCCCCCCCCCC\C=C\C OBDUMNZXAIUUTH-HWKANZROSA-N 0.000 description 1
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 1
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N Decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N Nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N Pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical group 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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
Description
一実施形態において、本発明は、内燃機関潤滑剤中の酸化防止剤としての式（１）の化合物（一般的には酒石酸誘導体）の用途を提供する。
本発明は、例えば以下の項目を提供する。
（項目１）
潤滑粘性の油、油溶性モリブデン化合物、および式（１）によって表される無灰磨耗防止剤を含む潤滑組成物
［式中、
ＹおよびＹ’は、独立して、−Ｏ−、＞ＮＨ、＞ＮＲ ３ であるか、または、ＹおよびＹ’基の両方を一緒にし、２つの＞Ｃ＝Ｏ基の間にＲ １ −Ｎ＜基を形成することによって形成されたイミド基であり、
Ｘは、独立して、−Ｚ−Ｏ−Ｚ’−、＞ＣＨ ２ 、＞ＣＨＲ ４ 、＞ＣＲ ４ Ｒ ５ 、＞Ｃ（ＯＨ）（ＣＯ ２ Ｒ ２ ）、＞Ｃ（ＣＯ ２ Ｒ ２ ） ２ 、＞ＣＣＨ ２ ＣＯ ２ Ｒ ２ または＞ＣＨＯＲ ６ であり、
ＺおよびＺ’は、独立して、＞ＣＨ ２ 、＞ＣＨＲ ４ 、＞ＣＲ ４ Ｒ ５ 、＞Ｃ（ＯＨ）（ＣＯ ２ Ｒ ２ ）、または＞ＣＨＯＲ ６ であり、
ｎは、０〜１０であり、ただし、ｎ＝１のとき、Ｘは＞ＣＨ ２ ではなく、ｎ＝２のとき、両方のＸが同時に＞ＣＨ ２ ではなく、
ｍは、０または１であり、
Ｒ １ は、独立して、水素または一般的に１〜１５０個の炭素原子を含有するヒドロカルビル基であり、ただし、Ｒ １ が水素であるとき、ｍは０であり、ｎは１以上であり、
Ｒ ２ は、一般的に１〜１５０個の炭素原子を含有するヒドロカルビル基であり、
Ｒ ３ 、Ｒ ４ およびＲ ５ は、独立して、ヒドロカルビル基またはヒドロキシ含有ヒドロカルビル基またはカルボキシル含有ヒドロカルビル基であり、
Ｒ ６ は、水素または一般的に１〜１５０個の炭素原子を含有するヒドロカルビル基である］。
（項目２）
前記式（１）の無灰の磨耗防止剤が、少なくとも１つのヒドロキシポリカルボン酸から誘導される、項目１に記載の潤滑組成物。
（項目３）
前記無灰の磨耗防止剤が、ヒドロキシポリカルボン酸ジエステル、ヒドロキシポリカルボン酸ジアミド、ヒドロキシポリカルボン酸イミド、ヒドロキシポリカルボン酸ジイミド、ヒドロキシポリカルボン酸エステルアミド、ヒドロキシポリカルボン酸エステルイミド、およびヒドロキシポリカルボン酸イミドアミドを含む、項目１に記載の潤滑組成物。
（項目４）
前記式（１）によって表される無灰の磨耗防止剤が、イミド、ジエステル、またはジアミドである、項目１に記載の潤滑組成物。
（項目５）
式（１）のＹおよびＹ’が両方とも−Ｏ−である、項目１に記載の潤滑組成物。
（項目６）
式（１）において、ｍが０または１、ｎが１〜２と定義され、Ｘが＞ＣＨＯＲ ６ であり、Ｒ １ 、Ｒ ２ およびＲ ６ が、独立して、水素または４〜３０個の炭素原子を含有するヒド
ロカルビル基である、項目１に記載の潤滑組成物。
（項目７）
前記無灰の磨耗防止剤が酒石酸またはクエン酸から誘導される、項目１に記載の潤滑組成物。
（項目８）
前記無灰の磨耗防止剤が前記潤滑組成物の０．０５〜１０重量％、または０．１〜５重量％で存在する、項目１に記載の潤滑組成物。
（項目９）
前記油溶性モリブデン化合物が、モリブデンジチオカルバメート類、モリブデンジアルキルジチオホスフェート類、モリブデン化合物のアミン塩類、モリブデンキサンテート類、モリブデン硫化物類、モリブデンカルボキシレート類、およびモリブデンアルコキシド類からなる群の少なくとも１員から選択される、項目１に記載の潤滑組成物。
（項目１０）
前記油溶性モリブデン化合物が、モリブデンジチオカルバメート類、モリブデンジアルキルジチオホスフェート類、およびモリブデン化合物のアミン塩類からなる群の少なくとも１員から選択される、項目９に記載の潤滑組成物。
（項目１１）
前記油溶性モリブデン化合物が、モリブデンジチオカルバメートである、項目１０に記載の潤滑組成物。
（項目１２）
前記油溶性モリブデン化合物が、０．５ｐｐｍ〜２０００ｐｐｍ、１ｐｐｍ〜７００ｐｐｍ、または２０ｐｐｍ〜２５０ｐｐｍのモリブデンを提供する量で存在する、項目１に記載の潤滑組成物。
（項目１３）
前記潤滑組成物が、（ｉ）０．８重量％以下の硫黄含量、（ｉｉ）０．２重量％以下のリン含量、または（ｉｉｉ）２重量％以下の硫酸塩灰分の少なくとも１つを有することをさらに特徴とする、項目１に記載の潤滑組成物。
（項目１４）
前記潤滑組成物が、（ｉ）０．５重量％以下の硫黄含量、（ｉｉ）０．１重量％以下のリン含量、および（ｉｉｉ）１．５重量％以下の硫酸塩灰分含量を有することを特徴とする、項目１に記載の潤滑組成物。
（項目１５）
摩擦調整剤（油溶性モリブデン化合物または式（１）の化合物以外のもの）、粘度調節剤、酸化防止剤（油溶性モリブデン化合物以外のもの）、過塩基性洗浄剤、スクシンイミド分散剤、またはそれらの混合物の少なくとも１つをさらに含む、項目１に記載の潤滑組成物。
（項目１６）
前記摩擦調整剤が、長鎖脂肪酸アミド類、長鎖脂肪酸エステル類、長鎖脂肪酸エポキシド誘導体類、長鎖脂肪酸イミダゾリン類、およびアルキルリン酸類のアミン塩類からなる群から選択される、項目１５に記載の潤滑組成物。
（項目１７）
リン含有磨耗防止剤をさらに含む、項目１に記載の潤滑組成物。
（項目１８）
過塩基性洗浄剤をさらに含む、項目１に記載の潤滑組成物。
（項目１９）
前記過塩基性洗浄剤が、非硫黄含有フェナート類、硫黄含有フェナート類、スルホネート類、サリキサレート類、サリチレート類、およびそれらの混合物からなる群から選択される、項目１８に記載の潤滑組成物。
（項目２０）
内燃機関を潤滑する方法であって、項目１に記載の前記潤滑組成物を前記内燃機関に
供給するステップを含む方法。
（項目２１）
潤滑剤中の酸化防止剤としての酒石酸誘導体の使用。
（項目２２）
前記酒石酸誘導体がタルトレートエステルである、項目２１に記載の使用。
In one embodiment, the present invention provides the use of a compound of formula (1) (generally a tartaric acid derivative) as an antioxidant in an internal combustion engine lubricant.
For example, the present invention provides the following items.
(Item 1)
Lubricating composition comprising an oil of lubricating viscosity, an oil-soluble molybdenum compound, and an ashless antiwear agent represented by formula (1)
[Where:
Y and Y ′ are independently —O—,>NH,> NR 3 , or both Y and Y ′ groups are taken together and R 1 — between two> C═O groups N <is an imide group formed by forming a group,
X is independently, -Z-O-Z '- ,> CH 2,> CHR 4,> CR 4 R 5,> C (OH) (CO 2 R 2),> C (CO 2 R 2) 2 ,> CCH 2 CO 2 R 2 or> CHOR 6 ;
Z and Z ′ are independently> CH 2 ,> CHR 4 ,> CR 4 R 5 ,> C (OH) (CO 2 R 2 ), or> CHOR 6 ;
n is 0-10, provided that when n = 1, X is not> CH 2 , and when n = 2, both X are not > CH 2 at the same time ,
m is 0 or 1,
R 1 is independently hydrogen or a hydrocarbyl group generally containing 1 to 150 carbon atoms, provided that when R 1 is hydrogen, m is 0 and n is 1 or more. ,
R 2 is a hydrocarbyl group generally containing 1 to 150 carbon atoms;
R 3 , R 4 and R 5 are independently a hydrocarbyl group or a hydroxy-containing hydrocarbyl group or a carboxyl-containing hydrocarbyl group;
R 6 is hydrogen or a hydrocarbyl group generally containing from 1 to 150 carbon atoms].
(Item 2)
The lubricating composition of item 1, wherein the ashless antiwear agent of formula (1) is derived from at least one hydroxypolycarboxylic acid.
(Item 3)
The ashless antiwear agent comprises hydroxypolycarboxylic acid diester, hydroxypolycarboxylic acid diamide, hydroxypolycarboxylic acid imide, hydroxypolycarboxylic acid diimide, hydroxypolycarboxylic acid ester amide, hydroxypolycarboxylic acid ester imide, and hydroxypolycarboxylic acid diamide. The lubricating composition according to item 1, comprising a carboxylic acid imidoamide.
(Item 4)
The lubricating composition according to item 1, wherein the ashless antiwear agent represented by the formula (1) is an imide, a diester, or a diamide.
(Item 5)
The lubricating composition according to item 1, wherein Y and Y ′ in formula (1) are both —O—.
(Item 6)
In formula (1), m is defined as 0 or 1, n is defined as 1-2, X is> CHOR 6 and R 1 , R 2 and R 6 are independently hydrogen or 4-30 Hydrides containing carbon atoms
The lubricating composition according to item 1, which is a locarbyl group.
(Item 7)
The lubricating composition of claim 1, wherein the ashless antiwear agent is derived from tartaric acid or citric acid.
(Item 8)
The lubricating composition of item 1, wherein the ashless antiwear agent is present at 0.05 to 10 wt%, or 0.1 to 5 wt% of the lubricating composition.
(Item 9)
The oil-soluble molybdenum compound is at least one member of the group consisting of molybdenum dithiocarbamates, molybdenum dialkyldithiophosphates, amine salts of molybdenum compounds, molybdenum xanthates, molybdenum sulfides, molybdenum carboxylates, and molybdenum alkoxides. The lubricating composition according to item 1, selected from:
(Item 10)
10. The lubricating composition according to item 9, wherein the oil-soluble molybdenum compound is selected from at least one member of the group consisting of molybdenum dithiocarbamates, molybdenum dialkyldithiophosphates, and amine salts of molybdenum compounds.
(Item 11)
Item 11. The lubricating composition according to Item 10, wherein the oil-soluble molybdenum compound is molybdenum dithiocarbamate.
(Item 12)
The lubricating composition according to item 1, wherein the oil-soluble molybdenum compound is present in an amount providing 0.5 ppm to 2000 ppm, 1 ppm to 700 ppm, or 20 ppm to 250 ppm molybdenum.
(Item 13)
The lubricating composition has at least one of (i) a sulfur content of 0.8% or less, (ii) a phosphorus content of 0.2% or less, or (iii) 2% or less sulfate ash. The lubricating composition according to item 1, further characterized by:
(Item 14)
The lubricating composition has (i) a sulfur content of 0.5 wt% or less, (ii) a phosphorus content of 0.1 wt% or less, and (iii) a sulfate ash content of 1.5 wt% or less. 2. The lubricating composition according to item 1, wherein
(Item 15)
Friction modifier (other than oil-soluble molybdenum compound or compound of formula (1)), viscosity modifier, antioxidant (other than oil-soluble molybdenum compound), overbased detergent, succinimide dispersant, or those The lubricating composition according to item 1, further comprising at least one of a mixture.
(Item 16)
Item 16. The friction modifier is selected from the group consisting of long-chain fatty acid amides, long-chain fatty acid esters, long-chain fatty acid epoxide derivatives, long-chain fatty acid imidazolines, and amine salts of alkyl phosphoric acids. Lubricating composition.
(Item 17)
The lubricating composition according to item 1, further comprising a phosphorus-containing antiwear agent.
(Item 18)
The lubricating composition of item 1, further comprising an overbased detergent.
(Item 19)
19. A lubricating composition according to item 18, wherein the overbased detergent is selected from the group consisting of non-sulfur containing phenates, sulfur containing phenates, sulfonates, salixates, salicylates, and mixtures thereof.
(Item 20)
A method of lubricating an internal combustion engine, wherein the lubricating composition according to item 1 is applied to the internal combustion engine.
A method comprising the step of providing.
(Item 21)
Use of tartaric acid derivatives as antioxidants in lubricants.
(Item 22)
Item 22. The use according to Item 21, wherein the tartaric acid derivative is a tartrate ester.
無灰の磨耗防止剤
一実施形態において、式（１）の化合物は、無灰の磨耗防止剤であり、それは酸化防止剤としても作用することができる。
Ashless Antiwear Agent In one embodiment, the compound of formula (1) is an ashless antiwear agent, which can also act as an antioxidant.
潤滑粘性の油
該潤滑組成物は、潤滑粘性の油を含む。かかる油類としては、天然および合成油、水素化分解、水素化、および水素化精製から生じた油、未精製、精製および再精製油およびそれらの混合物が挙げられる。
Oil of lubricating viscosity The lubricating composition comprises an oil of lubricating viscosity. Such oils include natural and synthetic oils, hydrocracked, hydrogenated, and hydrorefined oils, unrefined, refined and rerefined oils and mixtures thereof.
一実施形態において、該潤滑剤は、式（１）の化合物を採用するとき、フェノール系酸化防止剤を含有しない（または削減した量を含有する）。この実施形態は、式（１）の化合物が、フェノール系酸化防止剤類の部分的または完全な代替品として使用することができるために有益であり得る。第三ブチルフェノールの調製の間に、痕跡量の不純物トリス−ｔ−ブチルフェノールが形成され、最終生成物中に保持されるものと考えられる。トリス−ｔ−ブチルフェノールは、生物蓄積し、堆積物が積み重なって高く集中することが知られている。したがって、式（１）の化合物を酸化防止剤として採用することは、生物蓄積物を減少させる効果があり得る。
In one embodiment, the lubricant does not contain (or contains a reduced amount of) a phenolic antioxidant when employing the compound of formula (1). The exemplary type condition, the compounds of formula (1) is can be beneficial to be able to use as a partial or complete replacement of the phenolic antioxidant compound. During the preparation of tert-butylphenol, it is believed that trace amounts of impurities, tris-t-butylphenol, are formed and retained in the final product. Tris-t-butylphenol is known to bioaccumulate and deposits are highly concentrated. Therefore, employing a compound of formula (1) as an antioxidant can have the effect of reducing bioaccumulation.
硫化して硫化オレフィンを形成することができる適当なオレフィン類の例としては、プロピレン、ブチレン、イソブチレン、ペンテン、ヘキサン、ヘプテン、オクタン、ノネン、デセン、ウンデセン、ドデセン、ウンデシル、トリデセン、テトラデセン、ペンタデセン、ヘキサデセン、ヘプタデセン、オクタデセン、オクタデセネン（ｏｃｔａｄｅｃｅｎｅｎｅ）、ノノデセン（ｎｏｎｏｄｅｃｅｎｅ）、エイコセンまたはそれらの混合物が挙げられる。１実施態様において、ヘキサデセン、ヘプタデセン、オクタデセン、オクタデセネン、ノノデセン、エイコセンまたはそれらの混合物、およびそれらのダイマー、トリマーおよびテトラマーは、特に有用なオレフィン類である。あるいは、そのオレフィンは、ジエン、例えば、１，３−ブタジエンなど、と不飽和エステル、例えば、アクリル酸ブチルなど、とのディールス−アルダー付加物であり得る。
Examples of suitable olefins that can be sulfurized to form sulfurized olefins include propylene, butylene, isobutylene, pentene, hexane, heptene, octane, nonene, decene, undecene, dodecene, undecyl, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, Okutadesenen (octadecenene), Nonodesen (nonodecene), include eicosene or mixtures thereof. In one embodiment, hexadecene, heptadecene, octadecene, octadecenene, noodecene, eicosene or mixtures thereof, and their dimers, trimers and tetramers are particularly useful olefins. Alternatively, the olefin can be a Diels-Alder adduct of a diene, such as 1,3-butadiene, and an unsaturated ester, such as butyl acrylate.
一実施形態において該潤滑組成物は２−ストロークまたは４−ストロークの船舶ディーゼル内燃機関に適している。一実施形態において、該船舶ディーゼル内燃機関は２−ストロークエンジンである。本発明の該無灰の磨耗防止剤は、船舶ディーゼル潤滑組成物に、０．０１〜２０重量％、または０．０５〜１０重量％、または０．１〜５重量％で添加することができる。
In one embodiment, the lubricating composition is suitable for 2-stroke or 4-stroke marine diesel internal combustion engines. In one embodiment, the marine diesel internal combustion engine is a two-stroke engine. The ashless antiwear agent of the present invention is 0.01 to 20 wt%, or 0.05 to 10 wt%, or 0 . It can be added at 1 to 5% by weight.
Claims (15)
ＹおよびＹ’は、独立して、−Ｏ−、＞ＮＨ、＞ＮＲ３であるか、または、ＹおよびＹ’基の両方を一緒にし、２つの＞Ｃ＝Ｏ基の間にＲ１−Ｎ＜基を形成することによって形成されたイミド基であり、
Ｘは、独立して、−Ｚ−Ｏ−Ｚ’−、＞ＣＨ２、＞ＣＨＲ４、＞ＣＲ４Ｒ５、＞Ｃ（ＯＨ）（ＣＯ２Ｒ２）、＞Ｃ（ＣＯ２Ｒ２）２、＞ＣＣＨ２ＣＯ２Ｒ２または＞ＣＨＯＲ６であり、
ＺおよびＺ’は、独立して、＞ＣＨ２、＞ＣＨＲ４、＞ＣＲ４Ｒ５、＞Ｃ（ＯＨ）（ＣＯ２Ｒ２）、または＞ＣＨＯＲ６であり、
ｎは、０〜１０であり、ただし、ｎ＝１のとき、Ｘは＞ＣＨ２ではなく、ｎ＝２のとき、両方のＸが同時に＞ＣＨ２ではなく、
ｍは、０または１であり、
Ｒ１は、独立して、水素または一般的に１〜１５０個の炭素原子を含有するヒドロカルビル基であり、ただし、Ｒ１が水素であるとき、ｍは０であり、ｎは１以上であり、
Ｒ２は、一般的に１〜１５０個の炭素原子を含有するヒドロカルビル基であり、
Ｒ３、Ｒ４およびＲ５は、独立して、ヒドロカルビル基またはヒドロキシ含有ヒドロカルビル基またはカルボキシル含有ヒドロカルビル基であり、
Ｒ６は、水素または一般的に１〜１５０個の炭素原子を含有するヒドロカルビル基である］。 An oil of lubricating viscosity, an oil soluble molybdenum compound, and a lubricating composition comprising ashless antiwear agent represented by the formula (1)
Y and Y ′ are independently —O—,>NH,> NR 3 , or both Y and Y ′ groups together, R 2 — between two> C═O groups N <is an imide group formed by forming a group,
X is independently, -Z-O-Z '- ,> CH 2,> CHR 4,> CR 4 R 5,> C (OH) (CO 2 R 2),> C (CO 2 R 2) 2 ,> CCH 2 CO 2 R 2 or> CHOR 6 ;
Z and Z ′ are independently> CH 2 ,> CHR 4 ,> CR 4 R 5 ,> C (OH) (CO 2 R 2 ), or> CHOR 6 ;
n is 0-10, provided that when n = 1, X is not> CH 2 , and when n = 2, both X are not> CH 2 at the same time,
m is 0 or 1,
R 1 is independently hydrogen or a hydrocarbyl group generally containing 1 to 150 carbon atoms, provided that when R 1 is hydrogen, m is 0 and n is 1 or more. ,
R 2 is a hydrocarbyl group generally containing 1 to 150 carbon atoms;
R 3 , R 4 and R 5 are independently a hydrocarbyl group or a hydroxy-containing hydrocarbyl group or a carboxyl-containing hydrocarbyl group;
R 6 is hydrogen or a hydrocarbyl group generally containing from 1 to 150 carbon atoms].
供給するステップを含む方法。 A method of lubricating an internal combustion engine comprising the step of supplying the lubricating composition of claim 1 to the internal combustion engine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93994907P | 2007-05-24 | 2007-05-24 | |
| PCT/US2008/063671 WO2008147704A1 (en) | 2007-05-24 | 2008-05-15 | Lubricating composition containing ashfree antiwear agent based on hydroxypolycarboxylic acid derivative and a molybdenum compound |
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| Publication Number | Publication Date |
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| JP2010528156A JP2010528156A (en) | 2010-08-19 |
| JP2010528156A5 true JP2010528156A5 (en) | 2011-06-16 |
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| JP2010509454A Pending JP2010528156A (en) | 2007-05-24 | 2008-05-15 | Lubricating compositions containing ashless antiwear agents and molybdenum compounds based on hydroxypolycarboxylic acid derivatives |
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| Country | Link |
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| US (1) | US20100197536A1 (en) |
| EP (2) | EP2152838B1 (en) |
| JP (1) | JP2010528156A (en) |
| KR (1) | KR101496484B1 (en) |
| CN (1) | CN101679900A (en) |
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Families Citing this family (181)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2324101A1 (en) * | 2008-07-10 | 2011-05-25 | The Lubrizol Corporation | Carboxylic acid derivatives as friction modifiers in fuels |
| CN102165050A (en) * | 2008-09-26 | 2011-08-24 | 绿金润滑剂有限公司 | Lubricant composition and methods of manufacture thereof |
| CN102272275B (en) | 2008-11-05 | 2015-02-04 | 卢布里佐尔公司 | Method of lubricating an internal combustion engine |
| AU2009333576B2 (en) * | 2008-12-09 | 2016-05-26 | The Lubrizol Corporation | Lubricating composition containing a compound derived from a hydroxy-carboxylic acid |
| WO2010096291A1 (en) | 2009-02-18 | 2010-08-26 | The Lubrizol Corporation | Compounds and a method of lubricating an internal combustion engine |
| WO2010099136A1 (en) | 2009-02-26 | 2010-09-02 | The Lubrizol Corporation | Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant |
| EP2403930B1 (en) | 2009-03-03 | 2019-08-07 | The Lubrizol Corporation | Ashless or reduced ash quaternary detergents |
| JP5480259B2 (en) * | 2009-03-10 | 2014-04-23 | ザ ルブリゾル コーポレイション | Abrasion resistant composition and method for lubricating power transmission line devices |
| CA2761621A1 (en) * | 2009-05-13 | 2010-11-18 | The Lubrizol Corporation | Internal combustion engine lubricant |
| EP2430133B1 (en) | 2009-05-13 | 2015-07-08 | The Lubrizol Corporation | Method of lubricating with a composition containing a malic acid derivative |
| EP2438148B1 (en) * | 2009-06-04 | 2015-08-12 | The Lubrizol Corporation | Lubricating composition containing friction modifier and viscosity modifier |
| CN102482606B (en) | 2009-07-08 | 2014-07-02 | 卢布里佐尔公司 | Polymer blends useful as viscosity modifiers |
| CA2772116A1 (en) | 2009-08-18 | 2011-02-24 | The Lubrizol Corporation | Lubricating composition including a phosphite and a compound derived from a hydroxy-carboxylic acid |
| CN102575186A (en) | 2009-08-18 | 2012-07-11 | 卢布里佐尔公司 | Antiwear composition and method of lubricating driveline device |
| CA2772226A1 (en) | 2009-08-18 | 2011-02-24 | The Lubrizol Corporation | Lubricating composition containing an antiwear agent |
| US20120245065A1 (en) | 2009-08-18 | 2012-09-27 | The Lubrizol Corporation | Lubricating Composition Containing an Antiwear Agent |
| EP2467459A1 (en) | 2009-08-18 | 2012-06-27 | The Lubrizol Corporation | Antiwear composition and method of lubricating an internal combustion engine |
| CA2774124C (en) | 2009-09-14 | 2017-11-14 | The Lubrizol Corporation | Farm tractor lubricating composition with good water tolerance |
| WO2011034829A1 (en) | 2009-09-16 | 2011-03-24 | The Lubrizol Corporation | Lubricating composition containing an ester |
| US20120329694A1 (en) | 2009-11-24 | 2012-12-27 | The Lubrizol Corporation | Lubricating Composition Containing Viscosity Modifier Combination |
| WO2011066145A1 (en) * | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| US9528067B2 (en) * | 2009-11-30 | 2016-12-27 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| WO2011071756A1 (en) | 2009-12-07 | 2011-06-16 | The Lubrizol Corporation | Method of lubricating a manual transmission |
| EP2513270B1 (en) | 2009-12-14 | 2015-09-23 | The Lubrizol Corporation | Lubricating composition containing a nitrile compound |
| WO2011075403A1 (en) | 2009-12-14 | 2011-06-23 | The Lubrizol Corporation | Lubricating composition containing an antiwear agent |
| CN102782102B (en) | 2009-12-14 | 2014-09-24 | 卢布里佐尔公司 | Lubricating composition containing an antiwear agent |
| US9150813B2 (en) | 2009-12-17 | 2015-10-06 | The Lubrizol Corporation | Lubricating composition containing an aromatic compound |
| CN102791681B (en) | 2010-01-11 | 2015-05-27 | 路博润公司 | Overbased alkylated arylalkyl sulfonates |
| WO2011126736A1 (en) | 2010-04-06 | 2011-10-13 | The Lubrizol Corporation | Zinc salicylates for rust inhibition in lubricants |
| CA2796387A1 (en) | 2010-04-15 | 2011-10-20 | The Lubrizol Corporation | Low-ash lubricating oils for diesel engines |
| US9181510B2 (en) | 2010-05-20 | 2015-11-10 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
| SG185568A1 (en) | 2010-05-20 | 2012-12-28 | Lubrizol Corp | Lubricating composition containing a dispersant |
| SG185622A1 (en) | 2010-05-20 | 2012-12-28 | Lubrizol Corp | Low ash lubricants with improved seal and corrosion performance |
| CA2800503A1 (en) | 2010-05-24 | 2011-12-01 | The Lubrizol Corporation | Lubricating composition |
| US8969266B2 (en) | 2010-06-02 | 2015-03-03 | The Lubrizol Corporation | Lubricating composition containing a carboxylic functionalised polymer |
| MY161182A (en) | 2010-06-25 | 2017-04-14 | Castrol Ltd | Uses and compositions |
| WO2012027254A1 (en) | 2010-08-23 | 2012-03-01 | The Lubrizol Corporation | Lubricants containing aromatic dispersants and titanium |
| FR2964115B1 (en) * | 2010-08-27 | 2013-09-27 | Total Raffinage Marketing | ENGINE LUBRICANT |
| CA2809812A1 (en) | 2010-08-31 | 2012-03-08 | The Lubrizol Corporation | Lubricating composition containing an antiwear agent |
| WO2012030616A1 (en) | 2010-08-31 | 2012-03-08 | The Lubrizol Corporation | Star polymer and lubricating composition thereof |
| KR20130126608A (en) | 2010-10-06 | 2013-11-20 | 더루우브리졸코오포레이션 | Lubricating oil composition with anti-mist additive |
| WO2012056191A1 (en) | 2010-10-26 | 2012-05-03 | Castrol Limited | Non-aqueous lubricant and fuel compositions comprising fatty acid esters of hydroxy- carboxylic acids, and uses thereof |
| WO2012087781A1 (en) | 2010-12-21 | 2012-06-28 | The Lubrizol Corporation | Functionalized copolymers and lubricating compositions thereof |
| WO2012087773A1 (en) | 2010-12-21 | 2012-06-28 | The Lubrizol Corporation | Lubricating composition containing an antiwear agent |
| AU2011349660B2 (en) | 2010-12-21 | 2017-03-09 | The Lubrizol Corporation | Lubricating composition containing a detergent |
| CA2823623A1 (en) | 2011-01-04 | 2012-07-12 | The Lubrizol Corporation | Continuously variable transmission fluid with extended anti-shudder durability |
| US9347017B2 (en) | 2011-01-12 | 2016-05-24 | The Lubrizol Corporation | Engine lubricants containing a polyether |
| US9540582B2 (en) | 2011-02-16 | 2017-01-10 | The Lubrizol Corporation | Method of lubricating a driveline device |
| CN107502414A (en) | 2011-02-16 | 2017-12-22 | 路博润公司 | The method of lubricating composition and lubricating transmission system device |
| JP5840233B2 (en) | 2011-02-17 | 2016-01-06 | ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ | Lubricant with good TBN retention |
| BR112013023031A2 (en) | 2011-03-10 | 2016-12-13 | Lubrizol Corp | lubricating composition containing a thiocarbamate compound |
| US20140045734A1 (en) * | 2011-05-26 | 2014-02-13 | The Lubrizol Corporation | Stabilized Blends Containing Friction Modifiers |
| US9631160B2 (en) * | 2011-05-26 | 2017-04-25 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| CA2837102A1 (en) | 2011-06-15 | 2012-12-20 | The Lubrizol Corporation | Lubricating composition containing an ester of an aromatic carboxylic acid |
| CA2836598A1 (en) | 2011-06-15 | 2012-12-20 | The Lubrizol Corporation | Lubricating composition containing a salt of a carboxylic acid |
| ES2897493T3 (en) | 2011-06-21 | 2022-03-01 | Lubrizol Corp | Lubricant composition containing a dispersant |
| WO2012177537A1 (en) | 2011-06-21 | 2012-12-27 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
| JP2014522893A (en) | 2011-07-07 | 2014-09-08 | ザ ルブリゾル コーポレイション | Lubricant providing improved cleanliness for two stroke cycle engines |
| EP2768802A1 (en) | 2011-10-20 | 2014-08-27 | The Lubrizol Corporation | Bridged alkylphenol compounds |
| KR101994372B1 (en) | 2011-10-31 | 2019-06-28 | 더루우브리졸코오포레이션 | Ashless friction modifiers for lubricating compositions |
| CN104136589A (en) | 2011-12-29 | 2014-11-05 | 卢布里佐尔公司 | Limited slip friction modifiers for differentials |
| EP3088498A1 (en) | 2011-12-30 | 2016-11-02 | The Lubrizol Corporation | Use of star polymers |
| WO2013119623A1 (en) | 2012-02-08 | 2013-08-15 | The Lubrizol Corporation | Method of preparing a sulfurized alkaline earth metal dodecylphenate |
| US9321979B2 (en) * | 2012-03-13 | 2016-04-26 | Chemtura Corporation | Friction modifier composition for lubricants |
| US20160201004A1 (en) * | 2012-03-13 | 2016-07-14 | Chemtura Corporation | Friction modifier composition for lubricants |
| US20150024983A1 (en) * | 2012-03-26 | 2015-01-22 | The Lubrizol Corporation | Manual transmission lubricants with improved synchromesh performance |
| KR20140143823A (en) | 2012-04-04 | 2014-12-17 | 더루우브리졸코오포레이션 | Bearing lubricants for pulverizing equipment |
| US9217117B2 (en) | 2012-06-20 | 2015-12-22 | Castrol Limited | Friction modifier and their use in lubricants and fuels |
| PL2864458T3 (en) | 2012-06-20 | 2017-10-31 | Castrol Ltd | Friction modifier and their use in lubricants and fuels |
| EP2928994B1 (en) | 2012-12-07 | 2021-04-21 | The Lubrizol Corporation | Pyran dispersants |
| CN105143160B (en) | 2013-02-11 | 2018-11-20 | 路博润公司 | Bridging alkaline-earth metal alkyl phenate |
| KR20150124992A (en) | 2013-03-07 | 2015-11-06 | 더루우브리졸코오포레이션 | Limited slip friction modifiers for differentials |
| US9868919B2 (en) | 2013-03-12 | 2018-01-16 | The Lubrizol Corporation | Lubricating composition containing lewis acid reaction product |
| US9593292B2 (en) | 2013-03-13 | 2017-03-14 | The Lubrizol Corporation | Engine lubricants containing a polyether |
| CA2914045A1 (en) | 2013-05-30 | 2014-12-04 | The Lubrizol Corporation | Lubricating composition containing an oxyalkylated hydrocarbyl phenol |
| SG11201509216PA (en) * | 2013-05-30 | 2015-12-30 | Lubrizol Corp | Synergistic additive combination for industrial gear oils |
| EP3039096A1 (en) | 2013-09-10 | 2016-07-06 | The Lubrizol Corporation | Viscoelastic oil-based fluid and related methods |
| WO2015042340A1 (en) | 2013-09-19 | 2015-03-26 | The Lubrizol Corporation | Lubricant compositions for direct injection engines |
| EP3047001B1 (en) | 2013-09-19 | 2021-05-19 | The Lubrizol Corporation | Lubricant compositions for direct injection engines |
| CN103553907B (en) * | 2013-10-18 | 2015-09-23 | 湖南省华京粉体材料有限公司 | A kind of preparation method of oil-soluble organic molybdenum additive |
| EP3080169B1 (en) | 2013-12-10 | 2022-08-17 | The Lubrizol Corporation | Method for preparing functionalized graft polymers |
| KR102387026B1 (en) | 2013-12-19 | 2022-04-18 | 더루우브리졸코오포레이션 | Hydrogenated natural oils in rust preventive coatings |
| US9885004B2 (en) | 2013-12-23 | 2018-02-06 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
| US10190072B2 (en) | 2013-12-23 | 2019-01-29 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
| SG11201605533RA (en) | 2014-01-10 | 2016-08-30 | Lubrizol Corp | Method of lubricating an internal combustion engine |
| CA2936282C (en) | 2014-01-10 | 2022-06-07 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
| KR20160132906A (en) | 2014-03-11 | 2016-11-21 | 더루우브리졸코오포레이션 | Method of lubricating an internal combustion engine |
| KR20160132100A (en) | 2014-03-12 | 2016-11-16 | 더루우브리졸코오포레이션 | Method of lubricating an internal combustion engine |
| EP3116980B1 (en) | 2014-03-12 | 2023-04-26 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
| SG11201607626WA (en) | 2014-03-19 | 2016-10-28 | Lubrizol Corp | Lubricants containing blends of polymers |
| CA2944879A1 (en) | 2014-04-04 | 2015-10-08 | The Lubrizol Corporation | Method for preparing a sulfurized alkaline earth metal dodecylphenate |
| WO2015171674A1 (en) | 2014-05-06 | 2015-11-12 | The Lubrizol Corporation | Lubricant composition containing an antiwear agent |
| PL3514220T3 (en) | 2014-05-30 | 2020-09-07 | The Lubrizol Corporation | Low molecular weight amide/ester containing quaternary ammonium salts |
| EP3149127A1 (en) | 2014-05-30 | 2017-04-05 | The Lubrizol Corporation | High molecular weight imide containing quaternary ammonium salts |
| DK3511396T3 (en) | 2014-05-30 | 2020-08-31 | Lubrizol Corp | LOW MOLECULAR IMID CONTAINING QUATERAL AMMONIUM SALTS |
| CN106661473A (en) | 2014-05-30 | 2017-05-10 | 路博润公司 | Epoxide quaternized quaternary ammonium salts |
| US20170096611A1 (en) | 2014-05-30 | 2017-04-06 | The Lubrizol Corporation | Branched amine containing quaternary ammonium salts |
| US20170096610A1 (en) | 2014-05-30 | 2017-04-06 | The Lubrizol Corporation | High molecular weight amide/ester containing quaternary ammonium salts |
| EP3149123A2 (en) | 2014-05-30 | 2017-04-05 | The Lubrizol Corporation | Coupled quaternary ammonium salts |
| US20170114297A1 (en) | 2014-05-30 | 2017-04-27 | The Lubrizol Corporation | Imidazole containing quaternary ammonium salts |
| WO2015200592A1 (en) | 2014-06-27 | 2015-12-30 | The Lubrizol Corporation | Mixtures of friction modifiers to provide good friction performance to transmission fluids |
| EP3177700B1 (en) | 2014-08-06 | 2022-03-02 | The Lubrizol Corporation | Industrial gear lubricant with biodegradable sulfur component |
| US10611981B2 (en) | 2014-11-12 | 2020-04-07 | The Lubrizol Corporation | Mixed phosphorus esters for lubricant applications |
| EP3227417A1 (en) | 2014-12-03 | 2017-10-11 | The Lubrizol Corporation | Lubricating composition containing an oxyalkylated hydrocarbyl phenol |
| EP3227416A1 (en) | 2014-12-03 | 2017-10-11 | The Lubrizol Corporation | Lubricating composition containing an oxyalkylated aromatic polyol compound |
| CA2971185C (en) | 2014-12-15 | 2023-07-18 | The Lubrizol Corporation | Oxidized alpha-olefins in rust preventive coatings |
| EP3233782B1 (en) | 2014-12-15 | 2022-02-02 | The Lubrizol Corporation | Catalytic oxidation of hydrocarbons |
| WO2016099490A1 (en) | 2014-12-17 | 2016-06-23 | The Lubrizol Corporation | Lubricating composition for lead and copper corrosion inhibition |
| MX2017008387A (en) | 2014-12-29 | 2017-10-26 | Lubrizol Corp | Synergistic rust inhibitor combination for lubricating grease. |
| WO2016138248A1 (en) | 2015-02-26 | 2016-09-01 | The Lubrizol Corporation | Aromatic tetrahedral borate compounds for lubricating compositions |
| KR102608828B1 (en) * | 2015-02-26 | 2023-11-30 | 더루브리졸코오퍼레이션 | Aromatic detergents and lubricating compositions thereof |
| WO2016144880A1 (en) | 2015-03-09 | 2016-09-15 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
| JP2018512485A (en) | 2015-03-18 | 2018-05-17 | ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ | Lubricant composition for direct injection engines |
| US20160272915A1 (en) | 2015-03-18 | 2016-09-22 | The Lubrizol Corporation | Lubricant compositions for direct injection engines |
| EP3274428B1 (en) | 2015-03-25 | 2022-12-21 | The Lubrizol Corporation | Use of lubricant compositions for direct injection engines |
| EP3280787B1 (en) | 2015-04-09 | 2023-09-06 | The Lubrizol Corporation | Lubricants containing quaternary ammonium compounds |
| EP3307858B1 (en) | 2015-06-12 | 2021-06-09 | The Lubrizol Corporation | Michael adduct amino esters as total base number boosters for marine diesel engine lubricating compositions |
| ES2930218T3 (en) | 2015-07-10 | 2022-12-09 | Lubrizol Corp | Viscosity Modifiers to Improve Fluoroelastomer Seal Performance |
| EP3325585B1 (en) | 2015-07-20 | 2023-03-29 | The Lubrizol Corporation | Zinc-free lubricating composition |
| CA2995956A1 (en) | 2015-08-20 | 2017-02-23 | The Lubrizol Corporation | Azole derivatives as lubricating additives |
| EP3371284A1 (en) | 2015-11-06 | 2018-09-12 | The Lubrizol Corporation | Lubricant composition containing an antiwear agent |
| EP3371286A1 (en) | 2015-11-06 | 2018-09-12 | The Lubrizol Corporation | Lubricant composition containing an antiwear agent |
| KR20180083363A (en) | 2015-11-09 | 2018-07-20 | 더루브리졸코오퍼레이션 | Use of Quaternary Amine Additives to Improve Water Separation |
| CA3004729A1 (en) | 2015-11-11 | 2017-05-18 | The Lubrizol Corporation | Lubricating composition comprising thioether-substituted phenolic compound |
| CA3005091A1 (en) | 2015-11-17 | 2017-05-26 | The Lubrizol Corporation | Toxicologically acceptable alkylphenol detergents as friction modifiers in automotive lubricating oils |
| WO2017096175A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight imide containing quaternary ammonium salts having short hydrocarbon tails |
| WO2017096159A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails |
| US10975323B2 (en) | 2015-12-15 | 2021-04-13 | The Lubrizol Corporation | Sulfurized catecholate detergents for lubricating compositions |
| EP3778837B1 (en) | 2016-02-24 | 2024-01-17 | The Lubrizol Corporation | Use of lubricant compositions for direct injection engines |
| US20190062666A1 (en) | 2016-03-03 | 2019-02-28 | The Lubrizol Corporation | Lubricating Oil Composition Having Improved Air Release |
| CA3020122A1 (en) | 2016-04-07 | 2017-10-12 | The Lubrizol Corporation | Mercaptoazole derivatives as lubricating additives |
| US20190119594A1 (en) | 2016-04-20 | 2019-04-25 | The Lubrizol Corporation | Lubricant for two-stroke cycle engines |
| CN109415649B (en) | 2016-05-18 | 2022-11-08 | 路博润公司 | Hydraulic fluid composition |
| EP3255129B1 (en) | 2016-06-06 | 2024-01-24 | The Lubrizol Corporation | Thiol-carboxylic adducts as lubricating additives |
| WO2017218657A2 (en) | 2016-06-17 | 2017-12-21 | The Lubrizol Corporation | Polyisobutylene-substituted phenol, derivatives thereof, and lubricating compositions containing the polyisobutylene-substituted phenol and its derivatives |
| SG10202012642XA (en) | 2016-06-17 | 2021-01-28 | Lubrizol Corp | Lubricating compositions |
| SG11201810334SA (en) | 2016-06-17 | 2018-12-28 | Lubrizol Corp | Lubricating compositions |
| WO2017218662A1 (en) | 2016-06-17 | 2017-12-21 | The Lubrizol Corporation | Lubricating compositions |
| US10260019B2 (en) | 2016-06-30 | 2019-04-16 | The Lubrizol Corporation | Hydroxyaromatic succinimide detergents for lubricating compositions |
| KR102078435B1 (en) | 2016-07-14 | 2020-02-17 | 주식회사 엘지화학 | Organic light emitting diode and manufacturing method of the same |
| WO2018013451A1 (en) | 2016-07-15 | 2018-01-18 | The Lubrizol Corporation | Engine lubricants for siloxane deposit control |
| JP7402683B2 (en) | 2016-07-22 | 2023-12-21 | ザ ルブリゾル コーポレイション | Aliphatic tetrahedral borate compounds for lubricating compositions |
| US11427780B2 (en) | 2016-09-12 | 2022-08-30 | The Lubrizol Corporation | Total base number boosters for marine diesel engine lubricating compositions |
| CA3035071A1 (en) | 2016-09-14 | 2018-03-22 | The Lubrizol Corporation | Lubricating composition comprising sulfonate detergent and ashless hydrocarbyl phenolic compound |
| WO2018052692A1 (en) | 2016-09-14 | 2018-03-22 | The Lubrizol Corporation | Lubricating composition and method of lubricating an internal combustion engine |
| WO2018075147A1 (en) | 2016-10-17 | 2018-04-26 | The Lubrizol Corporation | Acid emulsifier technology for continuous mixed emulsified acid systems |
| ES2914785T3 (en) | 2016-12-27 | 2022-06-16 | Lubrizol Corp | Lubricant composition including N-alkylated dianiline |
| US11162048B2 (en) | 2016-12-27 | 2021-11-02 | The Lubrizol Corporation | Lubricating composition with alkylated naphthylamine |
| WO2019005738A1 (en) | 2017-06-27 | 2019-01-03 | The Lubrizol Corporation | Lubricating composition for and method of lubricating an internal combustion engine |
| US11359159B2 (en) | 2017-06-27 | 2022-06-14 | The Lubrizol Corporation | Lubricating composition containing a self-assembling polymethacrylate block copolymer and an ethylene-α-olefin copolymer |
| CA3069970A1 (en) | 2017-07-17 | 2019-01-24 | The Lubrizol Corporation | Low dispersant lubricant composition |
| SG11202000427RA (en) | 2017-07-17 | 2020-02-27 | Lubrizol Corp | Low zinc lubricant composition |
| EP3658654A1 (en) | 2017-07-24 | 2020-06-03 | Chemtool Incorporated | Extreme pressure metal sulfonate grease |
| CN111356756A (en) | 2017-11-28 | 2020-06-30 | 路博润公司 | Lubricant composition for high efficiency engines |
| WO2019112720A1 (en) | 2017-12-04 | 2019-06-13 | The Lubrizol Corporation | Alkylphenol detergents |
| WO2019118117A1 (en) | 2017-12-15 | 2019-06-20 | The Lubrizol Corporation | Alkylphenol detergents |
| CA3104063A1 (en) | 2018-06-22 | 2019-12-26 | The Lubrizol Corporation | Lubricating compositions for heavy duty diesel engines |
| CA3120104A1 (en) | 2018-11-16 | 2020-05-22 | The Lubrizol Corporation | Alkylbenzene sulfonate detergents |
| JP2022514478A (en) | 2018-12-10 | 2022-02-14 | ザ ルブリゾル コーポレイション | Lubricating composition with mixed dispersant additive package |
| WO2020263964A1 (en) | 2019-06-24 | 2020-12-30 | The Lubrizol Corporation | Continuous acoustic mixing for performance additives and compositions including the same |
| US11932825B2 (en) | 2019-09-26 | 2024-03-19 | The Lubrizol Corporation | Lubricating compositions and methods of operating an internal combustion engine |
| CA3152564A1 (en) | 2019-09-26 | 2021-04-01 | Craig J. Jones | Lubricating compositions and methods of operating an internal combustion engine |
| BR112022007221A2 (en) | 2019-10-15 | 2022-07-05 | Lubrizol Corp | FUEL EFFICIENT LUBRICANT COMPOSITION |
| JP2023508906A (en) | 2019-12-18 | 2023-03-06 | ザ ルブリゾル コーポレイション | polymer surfactant compound |
| CN115052958A (en) | 2020-02-04 | 2022-09-13 | 路博润公司 | Lubricating composition and method of operating an internal combustion engine |
| WO2021183230A1 (en) | 2020-03-12 | 2021-09-16 | The Lubrizol Corporation | Oil-based corrosion inhibitors |
| EP4150034B1 (en) | 2020-05-13 | 2024-03-13 | The Lubrizol Corporation | Lubricating composition for and method of lubricating an internal combustion engine |
| WO2021247428A1 (en) | 2020-06-01 | 2021-12-09 | The Lubrizol Corporation | Surface isolation resistance compatibility test system and method |
| CN113845946A (en) * | 2020-06-28 | 2021-12-28 | 中国石油化工股份有限公司 | Fuel additive, preparation method thereof and fuel composition |
| CA3193463A1 (en) | 2020-09-22 | 2022-03-31 | The Lubrizol Corporation | Diesel engine lubricating compositions and methods of use thereof |
| CN116685663A (en) | 2020-12-23 | 2023-09-01 | 路博润公司 | Benzazepine compounds as antioxidants for lubricating compositions |
| EP4314211A1 (en) | 2021-04-01 | 2024-02-07 | The Lubrizol Corporation | Zinc free lubricating compositions and methods of using the same |
| CA3227404A1 (en) | 2021-07-29 | 2023-02-02 | Zachary L. RODGERS | 1,4-benzoxazine compounds and lubricant compositions containing the same |
| CN117813365A (en) | 2021-08-19 | 2024-04-02 | 路博润公司 | Friction modifier having improved friction characteristics and lubricating composition containing the same |
| IT202100022328A1 (en) | 2021-08-25 | 2023-02-25 | Versalis Spa | METHOD FOR THE PREPARATION OF Ω-AMINO-CARBOXYLIC ACIDS AND THEIR DERIVATIVES. |
| WO2023133090A1 (en) | 2022-01-04 | 2023-07-13 | The Lubrizol Corporation | Compounds and lubricant compositions containing the same |
| WO2024006125A1 (en) | 2022-06-27 | 2024-01-04 | The Lubrizol Corporation | Lubricating composition and method of lubricating an internal combustion engine |
| WO2024019952A1 (en) | 2022-07-18 | 2024-01-25 | The Lubrizol Corporation | Deposit control compounds for lubricating compositions |
| WO2024030592A1 (en) | 2022-08-05 | 2024-02-08 | The Lubrizol Corporation | Processes for producing radically-functionalized pibsa product derivatives and compositions comprising same |
| WO2024030591A1 (en) | 2022-08-05 | 2024-02-08 | The Lubrizol Corporation | Processes for producing reaction products including quaternary ammonium salts |
| WO2024047447A1 (en) | 2022-09-01 | 2024-03-07 | The Lubrizol Corporation | Gelling agent for calcium sulfonate greases |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2365291A (en) * | 1941-05-26 | 1944-12-19 | Lubri Zol Corp | Stabilizing agents for hydrocarbon compositions and the like |
| US2443578A (en) * | 1944-10-13 | 1948-06-15 | Socony Vacuum Oil Co Inc | Mineral oil composition |
| DE1248643B (en) | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Process for the preparation of oil-soluble aylated amines |
| US4326972A (en) | 1978-06-14 | 1982-04-27 | The Lubrizol Corporation | Concentrates, lubricant compositions and methods for improving fuel economy of internal combustion engine |
| US4329449A (en) | 1978-09-01 | 1982-05-11 | A. E. Staley Manufacturing Company | Method of using recycled mother liquors to produce aldosides |
| US4234435A (en) | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
| US4237022A (en) * | 1979-10-01 | 1980-12-02 | The Lubrizol Corporation | Tartarimides and lubricants and fuels containing the same |
| FR2512458A1 (en) | 1981-09-10 | 1983-03-11 | Lubrizol Corp | COMPOSITIONS, CONCENTRATES, LUBRICATING COMPOSITIONS AND METHODS FOR INCREASING FUEL SAVINGS IN INTERNAL COMBUSTION ENGINES |
| US4692257A (en) * | 1981-09-22 | 1987-09-08 | Mobil Oil Corporation | Borated hydroxy-containing compositions and lubricants containing same |
| US4640787A (en) * | 1982-04-01 | 1987-02-03 | Phillips Petroleum Company | Gasoline compositions containing branched chain amines or derivatives thereof |
| US4478604A (en) * | 1982-04-01 | 1984-10-23 | Phillips Petroleum Company | Gasoline compositions containing branched chain amines or derivatives thereof |
| US4741848A (en) * | 1986-03-13 | 1988-05-03 | The Lubrizol Corporation | Boron-containing compositions, and lubricants and fuels containing same |
| US4758362A (en) | 1986-03-18 | 1988-07-19 | The Lubrizol Corporation | Carbamate additives for low phosphorus or phosphorus free lubricating compositions |
| US4952328A (en) * | 1988-05-27 | 1990-08-28 | The Lubrizol Corporation | Lubricating oil compositions |
| US4997969A (en) | 1988-12-12 | 1991-03-05 | The Lubrizol Corporation | Carbamate additives for lubricating compositions |
| US5038319A (en) | 1989-04-24 | 1991-08-06 | Xerox Corporation | System for recording and remotely accessing operating data in a reproduction machine |
| US5338470A (en) * | 1992-12-10 | 1994-08-16 | Mobil Oil Corporation | Alkylated citric acid adducts as antiwear and friction modifying additives |
| US5387251A (en) * | 1994-05-02 | 1995-02-07 | Rouse; Evan D. | Endless belt sanding block |
| US6573224B2 (en) * | 1997-01-03 | 2003-06-03 | Bardahl Manufacturing Corporation | Two-cycle engine lubricant composition comprising an ester copolymer and a diester |
| US6172013B1 (en) * | 1997-09-17 | 2001-01-09 | Exxon Chemical Patents Inc | Lubricating oil composition comprising trinuclear molybdenum compound and diester |
| US6559105B2 (en) | 2000-04-03 | 2003-05-06 | The Lubrizol Corporation | Lubricant compositions containing ester-substituted hindered phenol antioxidants |
| US7022653B2 (en) * | 2003-03-10 | 2006-04-04 | Infineum International Limited | Friction modifiers for engine oil composition |
| US8598097B2 (en) | 2003-04-24 | 2013-12-03 | The Lubrizol Corporation | Diesel lubricant low in sulfur and phosphorus |
| US7785769B2 (en) * | 2003-07-25 | 2010-08-31 | The United States of America as reprsented by the Secretary of the Navy | Immobilization of oligonucleotides and proteins in sugar-containing hydrogels |
| US7696136B2 (en) | 2004-03-11 | 2010-04-13 | Crompton Corporation | Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters |
| US7807611B2 (en) | 2004-10-12 | 2010-10-05 | The Lubrizol Corporation | Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof |
| US7651987B2 (en) | 2004-10-12 | 2010-01-26 | The Lubrizol Corporation | Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof |
-
2008
- 2008-05-15 WO PCT/US2008/063671 patent/WO2008147704A1/en active Application Filing
- 2008-05-15 CA CA2688098A patent/CA2688098C/en active Active
- 2008-05-15 US US12/598,104 patent/US20100197536A1/en not_active Abandoned
- 2008-05-15 KR KR1020097027028A patent/KR101496484B1/en active IP Right Grant
- 2008-05-15 EP EP08755509A patent/EP2152838B1/en active Active
- 2008-05-15 EP EP12158486.6A patent/EP2463358B1/en active Active
- 2008-05-15 JP JP2010509454A patent/JP2010528156A/en active Pending
- 2008-05-15 CN CN200880017335A patent/CN101679900A/en active Pending
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