JP6811006B2 - Hydrogen bond aggregates and lubricant compositions containing the aggregates - Google Patents
Hydrogen bond aggregates and lubricant compositions containing the aggregates Download PDFInfo
- Publication number
- JP6811006B2 JP6811006B2 JP2015106499A JP2015106499A JP6811006B2 JP 6811006 B2 JP6811006 B2 JP 6811006B2 JP 2015106499 A JP2015106499 A JP 2015106499A JP 2015106499 A JP2015106499 A JP 2015106499A JP 6811006 B2 JP6811006 B2 JP 6811006B2
- Authority
- JP
- Japan
- Prior art keywords
- aggregate
- formula
- aggregates
- present
- friction
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 29
- 239000000314 lubricant Substances 0.000 title claims description 22
- 239000001257 hydrogen Substances 0.000 title claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 title claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 239000002199 base oil Substances 0.000 claims description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 5
- CWYNKKGQJYAHQG-UHFFFAOYSA-N 4-pentylbenzoic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C=C1 CWYNKKGQJYAHQG-UHFFFAOYSA-N 0.000 claims description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005642 Oleic acid Substances 0.000 claims description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- 238000005299 abrasion Methods 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 20
- 239000003921 oil Substances 0.000 description 16
- 239000002562 thickening agent Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000010687 lubricating oil Substances 0.000 description 10
- 239000004519 grease Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000005461 lubrication Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 6
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- -1 frill Chemical group 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 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
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000005305 interferometry Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 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 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Description
本発明は、摩擦および摩耗を低減することのできる会合体と、該会合体を含有する摩擦及び摩耗低減剤と、該会合体を含有する潤滑油と、該会合体を含有する潤滑油組成物とに関する。 The present invention relates to an aggregate capable of reducing friction and wear, a friction and wear reducing agent containing the aggregate, a lubricating oil containing the aggregate, and a lubricating oil composition containing the aggregate. Regarding and.
近年、省エネルギー対策および二酸化炭素の排出規制のため、エンジンなどの機械における摩擦係数を低減することが求められている。多くの場合、摩擦低減には潤滑油が用いられている。潤滑油は相対運動する二面間に油膜を形成し直接接触を防ぐことで、摩擦・摩耗を低減している。しかし、摩擦係数を下げるために潤滑油の粘度を下げると、油膜厚さが薄くなり固体接触を起こし、摩擦係数の上昇および材料の摩耗が促進される。固体接触を防ぐ厚い油膜を確保し、低摩擦を得ることは一成分の潤滑油では原理的に不可能である。この課題を解決するために、各種の添加剤が用いられている。
摩擦を低減する摩擦調整剤や摩耗を防止する耐摩耗剤は、通常、重金属やリンを含むため、環境負荷の立場からはこれらの成分を低減することが望まれている。
本発明者は、これまでに、液晶(アルキルシアノビフェニル)が厚い油膜を形成し、かつ低摩擦係数を示すことを発見している(非特許文献1)。その理由として、分子内の平面構造が潤滑面に平行に配向し、分子間で滑りやすくなっていることを明らかにしている。
他方、水素結合による会合体を用いて、摩擦係数を上げることのできるトラクションドライブ用流体組成物が知られている(特許文献1)。
In recent years, it has been required to reduce the coefficient of friction in machines such as engines for energy saving measures and carbon dioxide emission regulations. Lubricants are often used to reduce friction. Lubricating oil reduces friction and wear by forming an oil film between two surfaces that move relative to each other and preventing direct contact. However, if the viscosity of the lubricating oil is lowered in order to lower the friction coefficient, the oil film thickness becomes thin and solid contact occurs, which promotes an increase in the friction coefficient and wear of the material. In principle, it is impossible to secure a thick oil film that prevents solid contact and obtain low friction with a single component lubricating oil. In order to solve this problem, various additives are used.
Friction modifiers that reduce friction and wear-resistant agents that prevent wear usually contain heavy metals and phosphorus, and it is desired to reduce these components from the standpoint of environmental load.
The present inventor has previously discovered that a liquid crystal (alkylcyanobiphenyl) forms a thick oil film and exhibits a low coefficient of friction (Non-Patent Document 1). It is clarified that the reason is that the planar structure in the molecule is oriented parallel to the lubrication surface and becomes slippery between the molecules.
On the other hand, there is known a fluid composition for traction drive capable of increasing the friction coefficient by using an aggregate formed by hydrogen bonds (Patent Document 1).
本発明は、重金属やリンを含まず、低摩擦及び耐摩耗を得ることができる会合体と、該会合体を含有する摩擦低減剤かつ耐摩耗剤と、該会合体を含有する潤滑油と、該会合体を含有する潤滑油組成物を提供することを課題とする。 The present invention comprises an aggregate that does not contain heavy metals or phosphorus and can obtain low friction and wear resistance, a friction reducing agent and an abrasion resistant agent containing the aggregate, and a lubricating oil containing the aggregate. An object of the present invention is to provide a lubricating oil composition containing the aggregate.
本発明により、以下の会合体と、該会合体を含有する摩擦低減剤かつ耐摩耗剤と、該会合体を含有する潤滑油と、該会合体を含有する潤滑油組成物を提供する:
1.式(1)又は式(1’)で表される化合物と、式(2)で表される化合物との会合体。
A−X (1)
A−Y−A’ (1’)
B−Z (2)
(式中、A、A’及びBは、同一でも異なっていても良く、置換又は無置換のフェニル基或いは窒素原子、酸素原子及び硫黄原子からなる群から選ばれるヘテロ原子を少なくとも一つ有する炭素数4〜6の芳香族複素環を表す。
X及びZは、同一でも異なっていても良く、X,Y及びZは、YとZとの間で或いはXとZとの間で水素結合を形成できる官能基を表す。)
2.式(1)で表される化合物が、式中Aが、炭素数1〜10の直鎖又は分岐アルキル基により置換されているか又は無置換のベンゼンであり、式中Xが、-OH、-COOH及びピリジル基からなる群から選ばれる化合物である前記1項記載の会合体。
3.式(1)で表される化合物が、安息香酸、2-メチル安息香酸、p-ペンチル安息香酸及び2-ヒドロキシピリジンからなる群から選ばれる前記1又は2項記載の会合体。
4.前記1〜3のいずれか1項記載の会合体を含む、摩擦低減剤かつ耐摩耗剤。
5.前記1〜3のいずれか1項記載の会合体を含む潤滑剤。
6.前記1〜3のいずれか1項記載の会合体と、基油とを含む潤滑剤組成物。
7.さらに添加剤を含有する、前記6項記載の潤滑剤組成物。
INDUSTRIAL APPLICABILITY The present invention provides the following aggregates, a friction reducing agent and an abrasion resistant agent containing the aggregates, a lubricating oil containing the aggregates, and a lubricating oil composition containing the aggregates:
1. 1. An assembly of a compound represented by the formula (1) or the formula (1') and a compound represented by the formula (2).
AX (1)
AYA'(1')
BZ (2)
(In the formula, A, A'and B may be the same or different, and may be a substituted or unsubstituted phenyl group or a carbon having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. Represents an aromatic heterocycle of equations 4-6.
X and Z may be the same or different, and X, Y and Z represent functional groups capable of forming hydrogen bonds between Y and Z or between X and Z. )
2. 2. The compound represented by the formula (1) is benzene in which A in the formula is substituted with a linear or branched alkyl group having 1 to 10 carbon atoms or is unsubstituted, and X in the formula is -OH,-. The aggregate according to the above item 1, which is a compound selected from the group consisting of COOH and a pyridyl group.
3. 3. The aggregate according to item 1 or 2 above, wherein the compound represented by the formula (1) is selected from the group consisting of benzoic acid, 2-methylbenzoic acid, p-pentylbenzoic acid and 2-hydroxypyridine.
4. A friction reducing agent and an abrasion resistant agent containing the aggregate according to any one of the above 1 to 3.
5. A lubricant containing the aggregate according to any one of the above 1 to 3.
6. A lubricant composition containing the aggregate according to any one of items 1 to 3 and a base oil.
7. Item 6. The lubricant composition according to Item 6, further containing an additive.
本発明の会合体は、厚い油膜を形成しながら低いトラクション係数を示すことができる。したがって、本発明の会合体は、重金属やリンを含まないから環境に負荷をかけることがなく、しかも摩擦を低減しながら耐摩耗効果を発揮する、優れた流体潤滑性を有する。本発明の会合体は、常温から80℃程度の高温まで広い温度範囲に亘って使用することができる。
如何なる理論にも拘束されるものではないが、分子内に平面構造を有する化合物が、潤滑場で平面構造が分子配向することにより、相対的に滑ることで低摩擦係数を得る。水素結合により2つ以上の分子が会合体を作り、その中に平面構造を得る。接触場は1GPa程度の高圧になっており、水素結合が高圧場で安定になること、すなわち会合体は接触場で安定になる(Takiwatari, Nanao, Mori, Lubrication Science, 26巻,1号(2014) 54-59.)。
The aggregate of the present invention can exhibit a low traction coefficient while forming a thick oil film. Therefore, since the aggregate of the present invention does not contain heavy metals or phosphorus, it does not impose a load on the environment, and has excellent fluid lubricity that exhibits a wear resistance effect while reducing friction. The aggregate of the present invention can be used over a wide temperature range from room temperature to a high temperature of about 80 ° C.
Without being bound by any theory, a compound having a planar structure in the molecule obtains a low coefficient of friction by relatively sliding due to the molecular orientation of the planar structure in the lubrication field. Two or more molecules form an aggregate by hydrogen bonding, and a planar structure is obtained in the aggregate. The contact field has a high pressure of about 1 GPa, and the hydrogen bond becomes stable in the high pressure field, that is, the aggregate becomes stable in the contact field (Takiwatari, Nanao, Mori, Lubrication Science, Vol. 26, No. 1 (2014). ) 54-59.).
〔会合体〕
本発明の会合体は、式(1)又は式(1’)で表される化合物と、式(2)で表される化合物との会合体である:
A−X (1)
A−Y−A’ (1’)
B−Z (2)
(式中、A、A’及びBは、同一でも異なっていても良く、置換又は無置換のフェニル基或いは窒素原子、酸素原子及び硫黄原子からなる群から選ばれるヘテロ原子を少なくとも一つ有する炭素数4〜6の芳香族複素環を表す。芳香族複素環としては、チエニル、フリル、ピリジル等があげられる。
X及びYは、同一でも異なっていても良く、X,Y及びZは、YとZとの間で或いはXとZとの間で水素結合を形成できる官能基を表す。)
[Assembly]
The aggregate of the present invention is an aggregate of a compound represented by the formula (1) or the formula (1') and a compound represented by the formula (2):
AX (1)
AYA'(1')
BZ (2)
(In the formula, A, A'and B may be the same or different, and may be a substituted or unsubstituted phenyl group or a carbon having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. It represents an aromatic heterocycle of the number 4 to 6. Examples of the aromatic heterocycle include thienyl, frill, pyridyl and the like.
X and Y may be the same or different, and X, Y and Z represent functional groups capable of forming hydrogen bonds between Y and Z or between X and Z. )
式中Aは、炭素数1〜10の直鎖又は分岐アルキル基により置換されているか又は無置換のベンゼンであるのが好ましい。炭素数1〜10の直鎖アルキル基により置換されているか又は無置換のベンゼンであるのがより好ましい。
式中Xは、-OH、-COOH及びピリジル基からなる群から選ばれるのが好ましい。
式(1)で表される化合物が、安息香酸、2-メチル安息香酸、p-ペンチル安息香酸及び2-ヒドロキシピリジンからなる群から選ばれるのが特に好ましい。なかでも、p-ペンチル安息香酸が好ましい。
In the formula, A is preferably benzene substituted or unsubstituted by a linear or branched alkyl group having 1 to 10 carbon atoms. More preferably, it is benzene substituted or unsubstituted by a linear alkyl group having 1 to 10 carbon atoms.
In the formula, X is preferably selected from the group consisting of -OH, -COOH and pyridyl groups.
It is particularly preferable that the compound represented by the formula (1) is selected from the group consisting of benzoic acid, 2-methylbenzoic acid, p-pentylbenzoic acid and 2-hydroxypyridine. Of these, p-pentylbenzoic acid is preferable.
式中A’は、炭素数1〜10の直鎖又は分岐アルキル基により置換されているか又は無置換のベンゼンであるのが好ましい。炭素数1〜10の直鎖アルキル基により置換されているか又は無置換のベンゼンであるのがより好ましい。
式中Yは、-NHCO-であるのが好ましい。
In the formula, A'preferably is benzene substituted or unsubstituted by a linear or branched alkyl group having 1 to 10 carbon atoms. More preferably, it is benzene substituted or unsubstituted by a linear alkyl group having 1 to 10 carbon atoms.
In the formula, Y is preferably -NHCO-.
式中Bは、炭素数1〜20の直鎖又は分岐アルキル基又はアルケニル基であるのが好ましい。炭素数1〜20の直鎖アルキル基又はアルケニル基であるのがより好ましい。
式中Zは、-OH、-COOH及びピリジル基からなる群から選ばれるのが好ましい。
式(2)で表される化合物が、炭素数1〜20の飽和又は不飽和の直鎖又は分岐脂肪酸であるのが好ましい。なかでも、オレイン酸が好ましい。
In the formula, B is preferably a linear or branched alkyl group or alkenyl group having 1 to 20 carbon atoms. It is more preferably a linear alkyl group or an alkenyl group having 1 to 20 carbon atoms.
Z in the formula is preferably selected from the group consisting of -OH, -COOH and pyridyl groups.
The compound represented by the formula (2) is preferably a saturated or unsaturated linear or branched fatty acid having 1 to 20 carbon atoms. Of these, oleic acid is preferable.
式(1)又は式(1’)で表される化合物と、式(2)で表される化合物とは、水素結合により会合体を形成するため、その混合比が、モル比にして1:0.5〜1:2であるのが好ましい。式(1)又は式(1’)で表される化合物が過剰になると、結晶が析出し、分離してしまうので好ましくない。モル比が1:0.9〜1:1.1であるのがより好ましい。モル比が1:1であるのが最も好ましい。 Since the compound represented by the formula (1) or the formula (1') and the compound represented by the formula (2) form an aggregate by hydrogen bonding, the mixing ratio thereof is 1: 1. It is preferably 0.5 to 1: 2. If the amount of the compound represented by the formula (1) or the formula (1') is excessive, crystals are precipitated and separated, which is not preferable. More preferably, the molar ratio is 1: 0.9 to 1: 1.1. Most preferably, the molar ratio is 1: 1.
本発明の会合体が、p-ペンチル安息香酸とオレイン酸との会合体であるか、2-ヒドロキシピリジンとオレイン酸との会合体であるか、2-メチル安息香酸とオレイン酸との会合体であるのが好ましい。とりわけ、これらの混合比がモル比にして1:1であるのが特に好ましい。 The aggregate of the present invention is an aggregate of p-pentylbenzoic acid and oleic acid, an aggregate of 2-hydroxypyridine and oleic acid, or an aggregate of 2-methylbenzoic acid and oleic acid. Is preferable. In particular, it is particularly preferable that the mixing ratio of these is 1: 1 in terms of molar ratio.
本発明の会合体は、例えば、式(2)で表される化合物に、式(1)又は式(1’)で表される化合物を添加し、式(1)又は式(1’)で表される化合物の融点以上に加熱し混合する(A法)か、又は極性溶媒(アセトンなど)に、式(1)又は式(1’)で表される化合物及び式(2)で表される化合物を溶解し単量体にしたのち、溶媒を蒸発除去する(B法)ことにより製造することができる。 In the aggregate of the present invention, for example, a compound represented by the formula (1) or the formula (1') is added to the compound represented by the formula (2), and the compound represented by the formula (1) or the formula (1') is added. The compound represented by the formula (1) or the formula (1') and the compound represented by the formula (2) are either heated and mixed above the melting point of the represented compound (method A) or in a polar solvent (acetone or the like). It can be produced by dissolving a compound to form a monomer and then evaporating and removing the solvent (method B).
本発明の会合体は、潤滑剤又は潤滑油として用いることができる。
本発明の会合体はまた、摩擦低減と耐摩耗の二重の作用を有する添加剤として用いることができる。前記会合体を添加剤として基油に含ませて潤滑剤組成物とすることもできる。このとき、潤滑剤組成物の全質量に対し、前記会合体を10〜60質量%含ませるのが好ましい。含有量に依存して摩擦係数は変化するが、10質量%未満では低摩擦及び耐摩耗効果が十分でない場合があり、60質量%を超えても効果を発揮するが経済的でない。30〜50質量%含ませるのがより好ましい。
The aggregate of the present invention can be used as a lubricant or a lubricating oil.
The aggregate of the present invention can also be used as an additive having a dual action of friction reduction and wear resistance. The aggregate may be included in the base oil as an additive to prepare a lubricant composition. At this time, it is preferable to include the aggregate in an amount of 10 to 60% by mass with respect to the total mass of the lubricant composition. The friction coefficient changes depending on the content, but if it is less than 10% by mass, the low friction and wear resistance effect may not be sufficient, and if it exceeds 60% by mass, the effect is exhibited, but it is not economical. It is more preferable to include 30 to 50% by mass.
〔基油〕
本発明の潤滑剤組成物に使用できる基油としては、鉱油のほか合成炭化水素油であるポリαオレフィンやポリブテン、エーテル系合成油であるアルキルジフェニルエーテルやポリプロピレングリコール、エステル系合成油であるジエステル、ポリオールエステル、その他シリコーン油やフッ素油など各種合成油が挙げられる。このうち、合成炭化水素油が好ましく、ポリαオレフィンがより好ましい。
本発明の潤滑剤組成物中の基油の含有量は、70〜95質量%であるのが好ましく、75〜90質量%であるのがより好ましい。
[Base oil]
Base oils that can be used in the lubricant composition of the present invention include mineral oils, polyα-olefins and polybutenes that are synthetic hydrocarbon oils, alkyldiphenyl ethers and polypropylene glycols that are ether-based synthetic oils, and diesters that are ester-based synthetic oils. Examples include polyol esters and other synthetic oils such as silicone oils and fluorine oils. Of these, synthetic hydrocarbon oils are preferred, and polyα-olefins are more preferred.
The content of the base oil in the lubricant composition of the present invention is preferably 70 to 95% by mass, more preferably 75 to 90% by mass.
本発明の会合体に増ちょう剤を加えるか、又は本発明の会合体と上記基油との混合物に増ちょう剤を加え、グリース組成物としても良い。本発明のグリース組成物を形成するのに使用できる増ちょう剤としては、金属石けん系増ちょう剤、ジウレアに代表されるウレア系増ちょう剤、有機化クレイやシリカに代表される無機系増ちょう剤、ポリテトラフルオロエチレン、及びメラミンシアヌレートに代表される有機系増ちょう剤から選ばれる少なくとも1種類である。ウレア系増ちょう剤と金属石けん系増ちょう剤が好ましい。ジウレア系増ちょう剤とリチウム石けん系増ちょう剤がより好ましい。 A thickener may be added to the aggregate of the present invention, or a thickener may be added to the mixture of the aggregate of the present invention and the above base oil to obtain a grease composition. Examples of the thickener that can be used to form the grease composition of the present invention include metallic soap-based thickeners, urea-based thickeners typified by diurea, and inorganic thickeners typified by organic clay and silica. At least one selected from agents, polytetrafluoroethylene, and organic thickeners typified by melamine cyanurate. Urea-based thickeners and metallic soap-based thickeners are preferred. Diurea-based thickeners and lithium soap-based thickeners are more preferred.
増ちょう剤の含有量は、本発明のグリース組成物の全質量を基準として、好ましくは3〜25質量%、より好ましくは5〜20質量%である。3質量%を下回ると、グリースが軟らかく、漏洩することがあり、十分な潤滑寿命を満足することができない場合がある。一方、25質量%より多いと流動性が劣るためグリースが潤滑部に入り込みにくくなり、十分な潤滑寿命を満足することができない場合がある。 The content of the thickener is preferably 3 to 25% by mass, more preferably 5 to 20% by mass, based on the total mass of the grease composition of the present invention. If it is less than 3% by mass, the grease is soft and may leak, and a sufficient lubrication life may not be satisfied. On the other hand, if it is more than 25% by mass, the fluidity is inferior, so that it becomes difficult for grease to enter the lubricated portion, and a sufficient lubrication life may not be satisfied.
本発明のグリース組成物の混和ちょう度は、好ましくは85〜475、より好ましくは160〜400である。混和ちょう度が475を上回ると漏洩が多くなり、十分な潤滑寿命を満足することができないことがある。一方、混和ちょう度が85を下回ると、グリースの流動性が悪くなり、十分な潤滑寿命を満足することができないことがある。 The mixing consistency of the grease composition of the present invention is preferably 85 to 475, more preferably 160 to 400. If the mixing consistency exceeds 475, leakage will increase and it may not be possible to satisfy a sufficient lubrication life. On the other hand, if the mixing consistency is less than 85, the fluidity of the grease deteriorates, and a sufficient lubrication life may not be satisfied.
また、必要に応じて各種添加剤を本発明の潤滑剤組成物又はグリース組成物に含ませることができる。このような添加剤としては、例えば、酸化防止剤、錆止め剤、金属腐食防止剤、油性剤、他の耐摩耗剤、極圧剤、ワックス、固体潤滑剤などがあげられる。本発明の潤滑剤組成物中のこれら添加剤の含有量は、通常、0.01〜30質量%である。 In addition, various additives can be included in the lubricant composition or grease composition of the present invention, if necessary. Examples of such additives include antioxidants, rust inhibitors, metal corrosion inhibitors, oily agents, other wear resistant agents, extreme pressure agents, waxes, solid lubricants and the like. The content of these additives in the lubricant composition of the present invention is usually 0.01 to 30% by mass.
本発明の潤滑剤組成物及びグリース組成物は、幅広い用途に用いることができる。例えば、転がり軸受、風車用軸受、自動車ハブユニット用軸受、ボールねじ、直動案内軸受、各種ギヤ、カム、等速ジョイント、ジャーナル軸受(滑り軸受)、自在継手、ピストン、ねじ、ワイヤーロープ、チェーン等があげられる。 The lubricant composition and grease composition of the present invention can be used in a wide range of applications. For example, rolling bearings, wind turbine bearings, automobile hub unit bearings, ball screws, linear motion guide bearings, various gears, cams, constant velocity joints, journal bearings (slip bearings), universal joints, pistons, screws, wire ropes, chains. And so on.
・実施例1、2、比較例1、2
下記表に示す会合体原料を用い、上記A法により会合体を調製した。
・実施例3〜6、比較例3,4
下記表に示す基油に、実施例1〜4及び比較例1〜3の会合体を添加し、混合することにより潤滑剤組成物を得た。
PAO:ポリαオレフィン (46.7Pa・s×10-3@25℃)
-Examples 1 and 2, Comparative Examples 1 and 2
The aggregate was prepared by the above method A using the aggregate raw materials shown in the table below.
-Examples 3 to 6, Comparative Examples 3 and 4
The aggregates of Examples 1 to 4 and Comparative Examples 1 to 3 were added to the base oils shown in the table below and mixed to obtain a lubricant composition.
PAO: Poly α-olefin (46.7 Pa · s × 10 -3 @ 25 ℃)
<粘度>
回転粘度計を使用して、実施例及び比較例の会合体及び潤滑剤組成物の粘度を測定することにより、油膜厚さを評価した。
(試験条件)
・25℃
<Viscosity>
The oil film thickness was evaluated by measuring the viscosities of the aggregates and lubricant compositions of Examples and Comparative Examples using a rotational viscometer.
(Test condition)
・ 25 ℃
<油膜厚>
また、PCS Instruments社EHL極薄膜計測システムを使用して、光干渉法により実施例5及び比較例1の油膜厚を実測した。
(試験条件)
荷重:20N
滑り率:0%
温度:25℃
ボール速度:0.29m/s
(試験結果)
実施例5の膜厚は108.4nmであった。
比較例1の膜厚は65.1nmであった。
参考のためPAO単独での油膜厚さを測定したところ、95.8nmであった。
<Oil film thickness>
Further, the oil film thicknesses of Example 5 and Comparative Example 1 were actually measured by the optical interferometry using the EHL ultrathin film measurement system manufactured by PCS Instruments.
(Test condition)
Load: 20N
Slip rate: 0%
Temperature: 25 ° C
Ball speed: 0.29m / s
(Test results)
The film thickness of Example 5 was 108.4 nm.
The film thickness of Comparative Example 1 was 65.1 nm.
For reference, the oil film thickness of PAO alone was measured and found to be 95.8 nm.
<トラクション係数測定方法>
ボールオンディスク型潤滑試験機を使用して、実施例及び比較例の会合体及び潤滑剤組成物のトラクション係数を測定した。
(試験条件)
ボール:SUJ2
ディスク:サファイア
荷重:20N
ボール速度:0.27m/s
滑り率:99%
温度:25℃
<Traction coefficient measurement method>
A ball-on-disk type lubrication tester was used to measure the traction coefficients of the aggregates and lubricant compositions of Examples and Comparative Examples.
(Test condition)
Ball: SUJ2
Disc: Sapphire Load: 20N
Ball speed: 0.27m / s
Slip rate: 99%
Temperature: 25 ° C
下記表に示した結果から、本発明の会合体及び本発明の会合体を含有する潤滑剤組成物は、厚い油膜を形成しながら低いトラクション係数を示すことが分かった。したがって、本発明の会合体及び本発明の会合体を含有する潤滑剤組成物は、摩擦を低減しながら耐摩耗効果を発揮する、優れた流体潤滑性をもつといえる。 From the results shown in the table below, it was found that the aggregate of the present invention and the lubricant composition containing the aggregate of the present invention show a low traction coefficient while forming a thick oil film. Therefore, it can be said that the aggregate of the present invention and the lubricant composition containing the aggregate of the present invention have excellent fluid lubricity, which exhibits a wear resistance effect while reducing friction.
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015106499A JP6811006B2 (en) | 2015-05-26 | 2015-05-26 | Hydrogen bond aggregates and lubricant compositions containing the aggregates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015106499A JP6811006B2 (en) | 2015-05-26 | 2015-05-26 | Hydrogen bond aggregates and lubricant compositions containing the aggregates |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016216692A JP2016216692A (en) | 2016-12-22 |
JP6811006B2 true JP6811006B2 (en) | 2021-01-13 |
Family
ID=57578720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015106499A Active JP6811006B2 (en) | 2015-05-26 | 2015-05-26 | Hydrogen bond aggregates and lubricant compositions containing the aggregates |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6811006B2 (en) |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10188267A (en) * | 1996-08-30 | 1998-07-21 | Sony Corp | Magnetic recording medium and cleaning tape |
JP4136474B2 (en) * | 2001-06-11 | 2008-08-20 | 富士フイルム株式会社 | Lubricant composition |
ITVA20080038A1 (en) * | 2008-06-30 | 2010-01-01 | Lamberti Spa | LIQUID THERMAL STABILIZERS FOR PVC |
JP2012077195A (en) * | 2010-10-01 | 2012-04-19 | National Institute Of Advanced Industrial Science & Technology | Method for adjusting viscosity of fluid organic substance, and viscosity adjusting agent for the same |
US9290715B2 (en) * | 2011-11-28 | 2016-03-22 | Shell Oil Company | Grease composition |
-
2015
- 2015-05-26 JP JP2015106499A patent/JP6811006B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2016216692A (en) | 2016-12-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI448549B (en) | Lubricant composition and lubricating system using same | |
JP5646859B2 (en) | Lubricating oil composition for continuously variable transmission | |
JP5109331B2 (en) | Grease composition | |
JP5350597B2 (en) | Grease composition and machine parts | |
JP5693240B2 (en) | Lubricating oil composition | |
JP6889664B2 (en) | Lubricant composition for resin and resin lubrication method | |
MX2011003154A (en) | Lubricant compositions. | |
US9096814B2 (en) | Lubricating grease composition | |
Barnhill et al. | Tribological bench and engine dynamometer tests of a low viscosity SAE 0W-16 engine oil using a combination of ionic liquid and ZDDP as anti-wear additives | |
JP2008239840A (en) | Lubricant composition and lubricating system using the same | |
US9206377B1 (en) | Solid lubricant blends for use in lubricating compositions | |
Guo et al. | Friction and wear properties of halogen-free and halogen-containing ionic liquids used as neat lubricants, lubricant additives and thin lubricant layers | |
JP2002371290A (en) | Grease composition for lubricating resin | |
RU2633350C1 (en) | Plastic antifriction high-temperature water-resistant lubricant | |
CA2838166C (en) | Extended service extreme pressure grease composition | |
JP6811006B2 (en) | Hydrogen bond aggregates and lubricant compositions containing the aggregates | |
CN107474912A (en) | A kind of high viscous finger, the Industrial gear oil composition of wide temperature range and its application | |
US20160272918A1 (en) | Synthetic anti-friction & extreme pressure metal conditioner composition and method of preparation | |
JP5286530B2 (en) | Grease composition and machine member | |
JP2005330328A (en) | Method of improving oil performance | |
JP6133148B2 (en) | Lubricating oil composition for drive system transmission | |
JP2020180249A (en) | Lubricant composition | |
JP5945657B2 (en) | Paste lubricant composition | |
JP2010254783A (en) | Lubricating oil | |
JP4602041B2 (en) | Grease composition with excellent fretting resistance |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180220 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20181130 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20181219 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190215 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190724 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20191016 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200116 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20200116 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20200124 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20200127 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20200306 |
|
C211 | Notice of termination of reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C211 Effective date: 20200316 |
|
C22 | Notice of designation (change) of administrative judge |
Free format text: JAPANESE INTERMEDIATE CODE: C22 Effective date: 20200601 |
|
C22 | Notice of designation (change) of administrative judge |
Free format text: JAPANESE INTERMEDIATE CODE: C22 Effective date: 20200803 |
|
C13 | Notice of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: C13 Effective date: 20200820 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20201014 |
|
C23 | Notice of termination of proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C23 Effective date: 20201105 |
|
C03 | Trial/appeal decision taken |
Free format text: JAPANESE INTERMEDIATE CODE: C03 Effective date: 20201203 |
|
C30A | Notification sent |
Free format text: JAPANESE INTERMEDIATE CODE: C3012 Effective date: 20201203 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20201214 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6811006 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |