JPH0377838B2 - - Google Patents
Info
- Publication number
- JPH0377838B2 JPH0377838B2 JP9049383A JP9049383A JPH0377838B2 JP H0377838 B2 JPH0377838 B2 JP H0377838B2 JP 9049383 A JP9049383 A JP 9049383A JP 9049383 A JP9049383 A JP 9049383A JP H0377838 B2 JPH0377838 B2 JP H0377838B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- carbon atoms
- oil
- hydrocarbon group
- represented
- 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.)
- Expired
Links
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 230000003449 preventive effect Effects 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 7
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000005260 corrosion Methods 0.000 description 14
- 230000007797 corrosion Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005536 corrosion prevention Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JTQQDDNCCLCMER-CLFAGFIQSA-N (z)-n-[(z)-octadec-9-enyl]octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCCCCCC\C=C/CCCCCCCC JTQQDDNCCLCMER-CLFAGFIQSA-N 0.000 description 1
- QELWBSUUOJGQHR-KHPPLWFESA-N (z)-nonadec-9-en-1-amine Chemical compound CCCCCCCCC\C=C/CCCCCCCCN QELWBSUUOJGQHR-KHPPLWFESA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 1
- BNDWRWFZSMPKQP-UHFFFAOYSA-N 3-pentadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC=CC1CC(=O)OC1=O BNDWRWFZSMPKQP-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- -1 alkylbenzotriazole Chemical compound 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- VVTGHWARMCSPKY-UHFFFAOYSA-N dodecan-1-amine;oxirane Chemical compound C1CO1.CCCCCCCCCCCCN VVTGHWARMCSPKY-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011346 highly viscous material Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DBIJGSRXWPQTLH-UHFFFAOYSA-N n-butyloctan-1-amine Chemical compound CCCCCCCCNCCCC DBIJGSRXWPQTLH-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- SDQCOADWEMMSGK-UHFFFAOYSA-N n-ethyloctan-1-amine Chemical compound CCCCCCCCNCC SDQCOADWEMMSGK-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical compound CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Description
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(Industrial Application Field) The present invention relates to an oil-soluble rust preventive agent that is added to lubricating oil and the like. (Prior art) Sulfur compounds, phosphorus compounds, chlorine compounds, etc. are generally used as additives added to lubricating oil to improve load-bearing performance.In practice, one or a combination of these compounds is used. has achieved its purpose. Among these, sulfur compounds have excellent load-bearing performance and are the most commonly used additives, but their biggest drawback is that they become more corrosive to metals in proportion to the amount of active sulfur in the ingredients. . Therefore, it is essential to use anticorrosive additives in order to prevent corrosion of metals, and compounds such as benzotriazole, alkylbenzotriazole, benzothiazole, dialkylthiourea, and alkylimidazole are used. However, since these anticorrosion additives generally have poor solubility in mineral oil, they have not yet achieved sufficient effectiveness in practice. In addition, as the performance of various mechanical devices such as cutting, rolling, drawing, and squeezing improves, there is a strong demand for improved load-bearing performance of the lubricating oils used, and the uses of additives containing active sulfur are gradually becoming more diverse. Tend. In addition, as the operating temperatures of various lubricating oils tend to rise gradually, there is a growing demand for improved corrosion prevention performance for metals. For example, benzotriazole, the most typical metal corrosion inhibitor, is conventionally used in lubricating oils by adding 1 to 5% by weight, but its heat resistance temperature is limited to 110 to 120 degrees Celsius, and the temperature range is higher than this. Almost no anti-corrosion performance can be expected. 2,5-dimercapto-1 used in the present invention,
3,4-thiadiazole (hereinafter abbreviated as DMTD)
is known as a metal corrosion inhibitor against active sulfur compounds, but this compound is water-soluble;
In this state, it cannot be used in mineral oil products because of its poor solubility in lubricating oil. Regarding oil solubilization of DMTD, for example, U.S. Pat.
It is described in No. 4301019 and No. 4210544. However, although the compounds described in these patent specifications seem to have good solubility in mineral oil, on the other hand, their anticorrosion performance against metals at high temperatures is insufficient or not observed at all. Another problem with DMTD is its strong odor. The odor of DMTD is due to the active moiety of the terminal group, that is, the mercaptan group, but if neutralization with a basic substance such as amine is performed to improve the odor, the anticorrosion performance may deteriorate or be completely removed. Disappear. (Object of the Invention) The present invention is intended to solve the above-mentioned conventional problems, and its purpose is to provide excellent anti-corrosion properties for metals even at high temperatures, and to provide substantially sufficient corrosion resistance to metals. The object of the present invention is to provide a rust preventive agent that is oil-soluble and has very little odor, and that can be used by adding it to lubricating oil. That is, the oil-soluble rust preventive agent of the present invention has the following formula: (A) General formula: [In the formula, R is a saturated or unsaturated hydrocarbon group having 4 to 22 carbon atoms or β having 4 to 22 carbon atoms
- represents a hydroxy hydrocarbon group, R 1 is a hydrogen atom or has 1 to 22 carbon atoms
represents a saturated or unsaturated hydrocarbon group, R 2 represents a hydrogen atom or a methyl group, and n
represents 0 or 1. ] and (B) general formula: [In the formula, R 3 represents a chain or cyclic hydrocarbon group having 4 to 18 carbon atoms, or a cyclic hydrocarbon group including a chain. ] and (C) the following formula: 2,5-dimercapto-1,3,
4-thiadiazole and (D) General formula: [In the formula, R 4 and R 5 represent a hydrogen atom or a saturated hydrocarbon group having 1 to 22 carbon atoms. ]
It is characterized by being a compound obtained by reacting an alkenylsuccinic anhydride represented by (Structure of the Invention) The oil-soluble rust preventive agent of the present invention can be obtained by the following manufacturing method. That is, 2 parts to 60 parts of the amine represented by the formula and 1 part to 30 parts of the glycidyl ether represented by the formula are added to a reaction vessel and heated to 60 to 90°C. When the epoxy group of the glycidyl ether starts ring-opening, an exothermic reaction occurs, so cooling is performed as necessary, and stirring is continued for 1 to 3 hours while controlling the temperature of the reactant to not exceed 120°C. Thus, a desired secondary or tertiary amine can be obtained. The reaction molar ratio of the amines represented by the formula and the glycidyl ether represented by the formula is appropriately from an equivalent amount of glycidyl ether to 1/4 of the equivalent amount,
The most preferred ratio is around 1/2 equivalent. DMTD is then added to the reaction. At this time, the reaction temperature is preferably 85 to 90°C, and the reaction time is 2 to 6 hours. The amount of DMTD added may be equal to or less than the equivalent amount to the secondary amine or tertiary amine. Thereafter, an alkenylsuccinic anhydride represented by the formula is added to neutralize excess secondary amine or tertiary amine. The amount of alkenylsuccinic anhydride added may exceed the equivalent amount to the amine. Since the compound obtained by the above reaction is a highly viscous substance with almost no fluidity at room temperature, it can be used after being dissolved in mineral oil, a sulfur-based extreme pressure additive, and fats and oils, if necessary. Examples of monoamines and diamines represented by the general formula used in the present invention include mono- and di-octylamine, mono- and di-decylamine, mono- and di-laurylamine, mono- and di-hexadecylamine. , mono- and di-
Oleylamine, mono- and di-stearylamine, monomethyloctylamine, monoethyloctylamine, monobutyloctylamine, monomethyloleylamine, monooctylamine (ethylene oxide or propylene oxide adduct), monolaurylamine (ethylene oxide or propylene oxide adduct) , monostearylamine (ethylene oxide or propylene oxide adduct), and similar primary amines, similar secondary amines. Examples of the glycidyl ether represented by the general formula used in the present invention include butyl glycidyl ether, allyl glycidyl ether, phenyl glycidyl ether, 2-ethylhexyl glycidyl ether, decyl glycidyl ether, and the like. Examples of the alkenylsuccinic anhydride represented by the general formula used in the present invention include dodecenylsuccinic anhydride and pentadecenylsuccinic anhydride. The oil-soluble rust preventive agent of the present invention can be manufactured by combining various compound components depending on the purpose of use and conditions of use as described above, and the following subgroups have particularly preferable characteristics: can be mentioned. (a) In the above formula, R has 6 or more carbon atoms.
represents 18 saturated or unsaturated hydrocarbon groups,
A compound in which R 1 and R 2 represent a hydrogen atom or a methyl group. (b) A compound in the above formula in which R 3 represents a saturated or unsaturated hydrocarbon group having 8 to 18 carbon atoms. (c) A compound in the above formula in which the groups R 4 and R 5 have a total number of carbon atoms of 9 to 19. Typically, R 5 is a methyl group, but is not limited thereto. The present invention provides a secondary or tertiary amine obtained from a primary or secondary amine and a glycidyl ether,
By making an addition reaction product of DMTD and further adding alkenylsuccinic anhydride, DMTD
It has succeeded in solving all the drawbacks of the prior art in the use of. In other words, addition reaction products obtained by directly reacting existing primary amines, secondary amines, and tertiary amines with DMTD have insufficient or no corrosion resistance against metals, but the products of the present invention Good corrosion resistance is observed. In addition, existing primary amines, secondary amines and tertiary amines
The addition reaction product obtained by directly reacting a class amine with DMTD lacks solubility in mineral oil and exhibits significant turbidity or separation phenomena, but the product of the present invention has good oil solubility. The odor of DMTD could be reduced or eliminated with the product of the present invention, as in the case of existing addition reaction products with amines. (Example) Examples of the oil-soluble rust preventive agent of the present invention will be described below. Example: A dodecylamine ethylene oxide adduct is used as the amine. The amine is heated slightly in advance to melt it, then 60 kg is taken out, charged into a reaction vessel, and heated to 90°C while stirring. Next, 25 kg of 2-ethylhexyl glycidyl ether was added as diglycidyl ether, and stirring was continued at 90°C for about 1.5 hours. Thereafter, heating is stopped, stirring is continued, and the temperature inside the reaction vessel is lowered to 75 to 80°C. The reaction state can be confirmed by separating a portion of the product and quantifying the amount of oxirane oxygen. This reaction was then treated with 2,5-dimercapto-1,3,4-thiadiazole (DMTD).
Add 1.7Kg of powder with stirring. A rapid exothermic reaction occurs and the viscosity increases, causing the liquid temperature to reach 90â.
Adjust the amount added so that it does not exceed. In this case, when the reaction temperature exceeds 95â, DMTD begins to decompose.
The reactants begin to become extremely colored. In addition, the reaction temperature must be strictly controlled because the decomposition products reduce the antirust ability of the product. After adding the entire amount of DMTD over about 20 minutes, stir at 90â for about 5 hours.
Dissolve the powder completely. Please note that if the reaction is incompletely dissolved, the product may become cloudy. Next, 55 kg of dodecenyl succinic anhydride is added and reacted at 90°C for about 1 hour. This is also an exothermic reaction, and the viscosity of the reactant increases as the reaction progresses. Adjust the amount added so that the reaction temperature does not exceed 95°C. By the above operations, the oil-soluble rust preventive of the present invention
141.7Kg is obtained. The oil-soluble rust preventive agent of the present invention shown in Table 1 below was obtained in a similar manner.
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(ã€) â
(ã) CH3â
(ã) C4H9â
(ã) C5H11â
(ã) C9H17â
(ã) C10H21â
(ã) C12H25â
(ã) C16H33â
(ãª) C18H37â
(ã)C18H35â
(ã«) C10H21âCHïŒOHïŒCH2â
(ãª) C12H25âCHïŒOHïŒCH2â
(ã¯) C14H29âCHïŒOHïŒCH2â
(ã«) C16H33âCHïŒOHïŒCH2â
(ãš)[Table] The formulas of the substituents of each component shown in Table 1 are as follows. (a) H- (b) CH 3 - (c) C 4 H 9 - (d) C 5 H 11 - (e) C 9 H 17 - (f) C 10 H 21 - (g) C 12 H 25 â (H) C 16 H 33 â (L) C 18 H 37 â (N)C 18 H 35 â (R) C 10 H 21 âCH(OH)CH 2 â (E) C 12 H 25 âCH( OH)CH 2 â (W) C 14 H 29 âCH(OH)CH 2 â (F) C 16 H 33 âCH(OH)CH 2 â (Y)
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(ã¿) C9H20
(ã¬) C12H28
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è¡šïŒã«ç€ºãã[Formula] (T) C 9 H 20 (R) C 12 H 28 The various mixtures obtained by the formulations shown in Table 1 are all brown and highly viscous at room temperature. Symbol G,
Although a mixture of U, V, and W has insufficient solubility in mineral oil as it is, it can be completely dissolved by using a solvent such as higher alcohol or higher glycol ether. Mixtures of other symbols have sufficient compatibility even when used alone. Comparative test of anticorrosion performance (1): A comparative test of the oil-soluble rust preventive agent of the present invention and the conventional rust preventive agent listed in Table 1 was conducted under the following conditions. In other words, the sulfur-based load-bearing performance improver
5% by weight of tertiary nonyl polysulfide (TNPS)
A machine oil 22 solution is used as a standard solution, and a known metal corrosion inhibitor and an oil-soluble rust inhibitor of the present invention are added to this solution in an amount of 0.1 to 100%.
Added 1.5wt% as a test liquid according to the test tube method of JIS-K2513 (Petroleum products copper plate corrosion test method).
A test was conducted at 100°C for 3 hours, and the corrosion state of the copper plate specimen was determined by comparing it with the copper plate corrosion standard specified in ASTM-D130. The results are shown in Table 2.
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ïŒãšåäžãšãããçµæãè¡šïŒã«ç€ºãã[Table] As is clear from the above table, all the rust inhibitors of the present invention exhibited excellent corrosion resistance. On the other hand, the only conventional anticorrosives showing comparable corrosion resistance were Nos. 1, 2, and 7. Comparative test of anticorrosion performance - (2) The performance of the anticorrosive agents that gave good results in Comparative Test 1 was evaluated by changing the test temperature. The test result is 110
â, 120â, 130â, 140â, and 150â, and the test time was 1 hour each. Other test conditions were the same as in Comparative Test 1. The results are shown in Table 3.
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èŒè©ŠéšïŒãšåäžãšãããçµæãè¡šïŒã«ç€ºãã[Table] From the above results, it can be seen that benzotriazole and tolyltriazole lose their anticorrosive effect in the high temperature range of 130°C or higher, whereas most of the rust inhibitors of the present invention show excellent anticorrosive effect up to 140°C. I understand. Corrosion prevention performance comparison test (3): Next, the effect on the corrosion prevention effect was investigated by varying the amount of the rust preventive of the present invention. The test temperature is 150â,
The test time was 1 hour. Other test conditions were the same as in Comparative Test 1. The results are shown in Table 4.
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ãªããªã©å€ãã®åªããå¹æãå¥ããã[Table] From the above results, it was found that by increasing the amount of the rust inhibitor of the present invention added, most of the rust inhibitors exhibited excellent corrosion prevention effects even in the high temperature range (150°C). Offensive odor comparison test: The rust inhibitor of the present invention is 2,5-dimercapto-
One of its characteristics is that it eliminates the mercaptan odor of 1,3,4-thiadiazole (DMTD) without impairing its antirust effect. Let's talk about comparative tests. Odor is a matter of human sensation, and it is extremely difficult to quantify its concentration or the difference between bad and good odor.One way to do this is to use the ``three-point comparison'' stipulated by the Tokyo Metropolitan Ordinance. The measurement was carried out according to the ``Style Smell Bag Method * ''. *March 1972 Tokyo Metropolitan Government Public Notice No. 238 Tokyo Metropolitan Pollution Prevention Ordinance Attached Table 4 7 Offensive Odor Section Note 2 The method prescribed by the governor The above method is a special plastic bag (formal name: Six women with a normal sense of odor were asked to use one odor bag (with a glass tube attached and a capacity of about 3) and two of the same plastic bags filled with odorless air. pick out a bag,
The odor concentration is determined by repeating the selection process while diluting the plastic bag containing the odor with odorless air, and taking the dilution ratio at which 4 out of 6 people were unable to make the selection. First, prepare two 1-reagent bottles, and apply the rust preventive agent of the present invention to one reagent pin and the other reagent pin.
After adding 200 ml of DMTD to each bag and leaving it at room temperature for 12 hours, the upper air layer was transferred to a special plastic bag and the odor concentration was measured using the above method. (Unable to select) DMTD became unmeasurable (unmeasurable due to the enormous dilution factor, probably hundreds of thousands of times or more), and it was found that the mercaptan odor of DMTD had almost disappeared. (Effect of the invention) As mentioned above, the oil-soluble rust preventive of the present invention has 2,5-
It further enhances the excellent anti-rust effect of dimercapto-1,3,4-thiadiazole (DMTD) and exhibits sufficient anti-rust effect even at high temperatures.It also has significantly improved oil solubility, making it suitable for various types of lubrication. Since it can be used by adding it to oil and is substantially odorless, it has many excellent effects such as not deteriorating the working environment.
Claims (1)
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éå€ã[Claims] 1 (A) General formula: [In the formula, R is a saturated or unsaturated hydrocarbon group having 4 to 22 carbon atoms or β having 4 to 22 carbon atoms
- represents a hydroxy hydrocarbon group, R 1 is a hydrogen atom or has 1 to 22 carbon atoms
represents a saturated or unsaturated hydrocarbon group, R 2 represents a hydrogen atom or a methyl group, and n represents 0 or 1. ] and (B) general formula: [In the formula, R 3 represents a chain or cyclic hydrocarbon group having 4 to 18 carbon atoms, or a cyclic hydrocarbon group including a chain. ] and (C) the following formula: 2,5-dimercapto-1,3,
4-thiadiazole and (D) General formula: [In the formula, R 4 and R 5 represent a hydrogen atom or a saturated hydrocarbon group having 1 to 22 carbon atoms. ]
An oil-soluble rust preventive agent comprising a compound obtained by reacting an alkenylsuccinic anhydride represented by: 2 In the above formula, R has 6 to 6 carbon atoms.
18 saturated or unsaturated hydrocarbon groups, R 1
An oil-soluble rust preventive agent comprising the compound according to claim 1, wherein represents a hydrogen atom or a methyl group. 3. An oil-soluble rust preventive agent comprising the compound according to claim 1, wherein in the above formula, R 2 represents a chain, ring, or chain-containing cyclic hydrocarbon group having 8 to 18 carbon atoms. 4. An oil-soluble rust inhibitor comprising the compound according to claim 1, wherein in the above formula, the total number of carbon atoms of the groups R 4 and R 5 is 9 to 19. 5 2 to 60 parts of the amine represented by the formula above, 1 to 30 parts of the glycidyl ether represented by the formula, 0.5 to 30 parts of 2,5-dimercapto-1,3,4-thiadiazole represented by the formula,
An oil-soluble rust inhibitor comprising the compound according to claim 1 obtained by reacting 1 to 100 parts of an alkenylsuccinic anhydride represented by the formula.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9049383A JPS59215394A (en) | 1983-05-23 | 1983-05-23 | Oil-soluble rust preventive |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9049383A JPS59215394A (en) | 1983-05-23 | 1983-05-23 | Oil-soluble rust preventive |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59215394A JPS59215394A (en) | 1984-12-05 |
JPH0377838B2 true JPH0377838B2 (en) | 1991-12-11 |
Family
ID=14000041
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9049383A Granted JPS59215394A (en) | 1983-05-23 | 1983-05-23 | Oil-soluble rust preventive |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59215394A (en) |
-
1983
- 1983-05-23 JP JP9049383A patent/JPS59215394A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS59215394A (en) | 1984-12-05 |
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