JPS6124438B2 - - Google Patents
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- Publication number
- JPS6124438B2 JPS6124438B2 JP11039280A JP11039280A JPS6124438B2 JP S6124438 B2 JPS6124438 B2 JP S6124438B2 JP 11039280 A JP11039280 A JP 11039280A JP 11039280 A JP11039280 A JP 11039280A JP S6124438 B2 JPS6124438 B2 JP S6124438B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- oil
- formula
- tetrazole
- oils
- 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
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- 239000006078 metal deactivator Substances 0.000 claims description 14
- 150000003536 tetrazoles Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 2 -ethyl-hexyl Chemical group 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000010723 turbine oil Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000010720 hydraulic oil Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004079 stearyl 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])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 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- VMTZSBMDTWQJSX-UHFFFAOYSA-N 2-ethyl-n-(2-ethylhexyl)-n-(tetrazol-5-ylidenemethyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)C=C1N=NN=N1 VMTZSBMDTWQJSX-UHFFFAOYSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000010718 automatic transmission oil Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010725 compressor oil Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=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
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000010711 gasoline engine oil Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000001050 lubricating effect Effects 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
- 238000005555 metalworking Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000010731 rolling oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
本発明は、金属不活性化剤およびその組成物に
関する。詳しくは、潤滑油添加剤として好ましく
使用され、新規な構造を有する金属不活性化剤お
よびその組成物に関する。
金属不活性化剤とは、燃料や潤滑油の酸化を促
進する溶解金属塩を不活性化し、あるいは金属表
面に不活性膜をつくる添加剤であり、ベンゾトリ
アゾール、その誘導体、あるいはチアジアゾール
などが広く知られているが、これらの化合物を使
用した場合の性能は必ずしも十分なものとはいえ
なかつた。本願発明者らは、数多くの化合物の合
成探索を行つた結果、特定された構造を有するテ
トラゾール誘導体が、従来より公知の上記化合物
に比べすぐれた性能を有することを見出し、本願
発明の完成に致つた。
すなわち本発明は、式（）；
および式（）；
から成る群より選ばれる少なくとも１種のテトラ
ゾール誘導体から成る金属不活性化剤に関する。
ここで、式（）および式（）において、
R1、R2およびR3は同種でも異種でもよく、C1〜
C20アルキル基、C2〜C20アルケニル基、C5〜C12
シクロアルキル基、C6〜C10アリール基、C7〜C9
アラルキル基、あるいはR4O（R5O）oR6〔R4は水
素原子またはC1〜C20アルキル基、R5、R6はC2〜
C3アルキレン基、ｎは０〜４〕で表わされる基
である。
以下、本発明による金属不活性化剤についてよ
り具体的に述べる。
式（）および（）において、R1、R2およ
びR3は同種でも異種でもよい。すなわち式
（）の化合物を用いる場合、R1およびR2は同種
でも異種でもよく、式（）の化合物と式（）
の化合物との混合物を用いる場合、R1、R2およ
びR3は同種でも異種でもよい。
R1〜R3のいずれかまたは２つ以上がアルキル
基の場合、C1〜C20、より好ましくはC3〜C18ア
ルキル基が使用され、好ましい具体例は、ブチ
ル、ヘキシル、オクチル、２−エチル−ヘキシ
ル、デシル、ドデシル、ヘキサデシルあるいはオ
クタデシル基である。
R1〜R3のいずれかまたは２つ以上がアルケニ
ル基の場合、C2〜C20、より好ましくは、C3〜
C18アルケニル基が使用され、好ましい具体例
は、ブテニル、オクテニル、デセニル、ドデセニ
ル、テトラデセニルおよびオクタデセニル（オレ
イル）基である。
R1〜R3のいずれかまたは２つ以上がシクロア
ルキル基の場合、C5〜C12シクロアルキル基が使
用され、好ましい具体例は、シクロヘキシル基で
ある。
R1〜R3のいずれかまたは２つ以上がアリール
基の場合、C6〜C10アリール基が使用され、好ま
しい具体例は、フエニルおよびナフチル基であ
る。
R1〜R3のいずれかまたは２つ以上がアラルキ
ル基の場合、C7〜C9アラルキル基が使用され、
好ましい具体例は、ベンジル基である。
R1〜R3のいずれかまたは２つ以上がR4O
（R5O）oR6で表わされる基の場合、R4は水素原子
またはC1〜C20アルキル基、好ましくは水素原子
またはC1〜C8アルキル基、更に好ましくは水素
原子であり、R5、R6はC2〜C3アルキレン基、ｎ
は０〜４、より好ましくは０である。好ましい具
体例は、ヒドロキシエチル、メトキシエチル、ｎ
−ブトキシエチル、メトキシエトキシエチル、ｎ
−ブトキシエトキシエチルおよびｎ−オクチルオ
キシプロピルオキシ基である。
本発明におけるテトラゾール誘導体の製造法
は、特に限定されないが、例えば式（）の化合
物を得るためには、テトラゾール、前記R1およ
びR2の条件を満足する２級アミンおよびホルム
アルデヒドのマンニツヒ反応が好ましく、式
（）の化合物を得るためには、テトラゾール、
前記R3の条件を満足する１級アミンおよびホル
ムアルデヒドのマンニツヒ反応が好ましい。
上記本発明による金属不活性化剤のうち、より
好ましいものは式（）で示される化合物であ
り、特にR1、R2が同種もしくは異種で、ヘキシ
ル、オクチル、デシル、ドデシル、ヘキサデシ
ル、オクタデシル基のものである。
本発明による金属不活性化剤は潤滑油に好まし
く使用されるものであり、好ましい潤滑油組成物
は、前記金属不活性化剤0.001〜10.0重量％、好
ましくは0.01〜1.0重量％を含有し、残部の全部
もしくは主要部が動粘度10〜10000cst（40℃）、
好ましくは20〜1000cst（40℃）、粘度指数80以
上、好ましくは90以上の鉱油および／または合成
油である組成物である。ここで鉱油としては、石
油の潤滑留分を水素化精製、白土精製、溶剤精製
あるいはこれらの組合せにより精製したものが好
ましく使用される。また合成油としては、ポリブ
テン、ポリ−α−オレフイン、ジエステル、ポリ
オールエステルあるいはこれらの混合物が好まし
く使用される。前記金属不活性化剤が0.001重量
％より少ない場合は金属不活性化剤としての所期
の効果を発揮し得ず、また10.0重量％より多い場
合は経済的に好ましくない。
また上記の潤滑油組成物において、必要に応じ
て、前記金属不活性化剤の他に、更に酸化防止
剤、清浄分散剤、粘度指数向上剤、流動点降下
剤、さび止め剤、極圧剤、油性向上剤あるいは消
泡剤などを配合することもできる。これらの各種
添加剤の詳細については、例えば潤滑学会誌15巻
６号あるいは桜井俊男編著「石油製品添加剤」
（幸書房）に開示されている。
本発明による金属不活性化剤は、潤滑油に好ま
しく使用されるものであり、具体的には、タービ
ン油、作動油、ギア油、ガソリンエンジン油、デ
イーゼルエンジン油、舶用エンジン油、圧縮機
油、油膜軸受油、冷凍機油、すべり案内面潤滑
油、圧延油、工作機械油、自動変速機油、各種金
属加工油あるいはグリースなどに使用され、さら
に電気絶縁油、熱媒体油あるいはさび止め油など
にも使用される。
以下、合成例、実施例および比較例により、本
発明をより具体的に説明する。
合成例
テトラゾール7.0ｇおよびビス（２−エチルヘ
キシル）アミン24.1ｇをとり、メタノール150ml
を加え、窒素気流中で撹拌した。ここに35％ホル
マリン水溶液10.4mlを滴下し、25℃において１時
間反応を行つた後、メタノール存在下で５時間還
流した。反応終了後、生成物をろ過し、メタノー
ルを除去した後、ｎ−ヘキサンを加え、ｎ−ヘキ
サン可溶分を回収して〔ビス（２−エチルヘキシ
ル）アミノメチレン〕−１・２・３・４−テトラ
ゾール（式（）において、R1、R2ともに２−
エチルヘキシル基である化合物）26.5ｇを得た。
以下同様に、マンニツヒ反応により、式（）で
表わさせるテトラゾール誘導体１〜12、および式
（）で表わされるテトラゾール誘導体13〜15を
合成した。
The present invention relates to metal deactivators and compositions thereof. Specifically, the present invention relates to a metal deactivator having a novel structure and a composition thereof, which is preferably used as a lubricating oil additive. Metal deactivators are additives that inactivate dissolved metal salts that promote oxidation of fuels and lubricating oils, or create inert films on metal surfaces. Widely used are benzotriazole, its derivatives, and thiadiazole. Although known, the performance when using these compounds was not necessarily sufficient. As a result of searching for the synthesis of a large number of compounds, the present inventors discovered that a tetrazole derivative having the specified structure has superior performance compared to the conventionally known above-mentioned compounds, and thus completed the present invention. Ivy. That is, the present invention is based on the formula (); and expression (); A metal deactivator comprising at least one tetrazole derivative selected from the group consisting of: Here, in formula () and formula (),
R 1 , R 2 and R 3 may be the same or different, and C 1 to
C20 alkyl group, C2 - C20 alkenyl group, C5 - C12
Cycloalkyl group, C6 - C10 aryl group, C7 - C9
Aralkyl group, or R 4 O (R 5 O) o R 6 [R 4 is a hydrogen atom or a C 1 - C 20 alkyl group, R 5 and R 6 are C 2 -
C 3 alkylene group, n is 0 to 4]. Hereinafter, the metal deactivator according to the present invention will be described in more detail. In formulas () and (), R 1 , R 2 and R 3 may be the same or different. That is, when using a compound of formula (), R 1 and R 2 may be the same or different, and the compound of formula () and the formula ()
When using a mixture with a compound, R 1 , R 2 and R 3 may be the same or different. When any or more of R 1 to R 3 is an alkyl group, a C 1 to C 20 , more preferably a C 3 to C 18 alkyl group is used, and preferred specific examples include butyl, hexyl, octyl, 2 -ethyl-hexyl, decyl, dodecyl, hexadecyl or octadecyl group. When one or more of R 1 to R 3 is an alkenyl group, C 2 to C 20 , more preferably C 3 to
C 18 alkenyl groups are used, preferred examples being butenyl, octenyl, decenyl, dodecenyl, tetradecenyl and octadecenyl (oleyl) groups. When any or more of R1 to R3 is a cycloalkyl group, a C5 to C12 cycloalkyl group is used, and a preferred specific example is a cyclohexyl group. When any or more of R 1 to R 3 is an aryl group, a C 6 to C 10 aryl group is used, and preferred specific examples are phenyl and naphthyl groups. When any or more of R 1 to R 3 is an aralkyl group, a C 7 to C 9 aralkyl group is used,
A preferred example is a benzyl group. Any or more of R 1 to R 3 is R 4 O
In the case of a group represented by ( R5O ) oR6 , R4 is a hydrogen atom or a C1 - C20 alkyl group, preferably a hydrogen atom or a C1 - C8 alkyl group, more preferably a hydrogen atom, R 5 and R 6 are C 2 to C 3 alkylene groups, n
is 0 to 4, more preferably 0. Preferred specific examples are hydroxyethyl, methoxyethyl, n
-butoxyethyl, methoxyethoxyethyl, n
-butoxyethoxyethyl and n-octyloxypropyloxy groups. The method for producing the tetrazole derivative in the present invention is not particularly limited, but for example, in order to obtain the compound of formula (), the Mannitz reaction of tetrazole, a secondary amine that satisfies the conditions of R 1 and R 2 , and formaldehyde is preferred. , to obtain the compound of formula (), tetrazole,
A Mannitz reaction of a primary amine and formaldehyde that satisfies the above-mentioned condition R3 is preferred. Among the metal deactivators according to the present invention, more preferred are compounds represented by the formula (), in particular, R 1 and R 2 are the same or different, hexyl, octyl, decyl, dodecyl, hexadecyl, octadecyl group. belongs to. The metal deactivator according to the invention is preferably used in lubricating oils, and preferred lubricating oil compositions contain 0.001 to 10.0% by weight, preferably 0.01 to 1.0% by weight of the metal deactivator, All or the main part of the remainder has a kinematic viscosity of 10 to 10,000cst (40℃),
Preferably, the composition is a mineral oil and/or synthetic oil having a viscosity index of 20 to 1000 cst (40° C.) and 80 or more, preferably 90 or more. The mineral oil preferably used here is one obtained by refining a lubricating fraction of petroleum by hydrorefining, clay refining, solvent refining, or a combination thereof. As the synthetic oil, polybutene, poly-α-olefin, diester, polyol ester, or a mixture thereof is preferably used. If the amount of the metal deactivator is less than 0.001% by weight, the desired effect as a metal deactivator cannot be exhibited, and if it is more than 10.0% by weight, it is economically unfavorable. In the above lubricating oil composition, in addition to the metal deactivator, if necessary, an antioxidant, a detergent dispersant, a viscosity index improver, a pour point depressant, a rust inhibitor, an extreme pressure agent, etc. , an oiliness improver or an antifoaming agent may also be added. For details on these various additives, see, for example, the Journal of the Japan Society of Lubrication, Vol. 15, No. 6, or "Petroleum Product Additives" edited by Toshio Sakurai.
(Saiwai Shobo). The metal deactivator according to the present invention is preferably used in lubricating oils, specifically turbine oils, hydraulic oils, gear oils, gasoline engine oils, diesel engine oils, marine engine oils, compressor oils, Used in oil film bearing oil, refrigeration machine oil, sliding guideway lubricating oil, rolling oil, machine tool oil, automatic transmission oil, various metal working oils and greases, as well as electrical insulation oil, heat transfer oil, rust prevention oil, etc. used. Hereinafter, the present invention will be explained in more detail with reference to Synthesis Examples, Examples, and Comparative Examples. Synthesis example: Take 7.0g of tetrazole and 24.1g of bis(2-ethylhexyl)amine, and add 150ml of methanol.
was added and stirred in a nitrogen stream. 10.4 ml of a 35% formalin aqueous solution was added dropwise thereto, the reaction was carried out at 25°C for 1 hour, and then refluxed for 5 hours in the presence of methanol. After the reaction was completed, the product was filtered, methanol was removed, n-hexane was added, and the n-hexane soluble content was collected to give [bis(2-ethylhexyl)aminomethylene]-1, 2, 3, 4 -tetrazole (in formula (), both R 1 and R 2 are 2-
26.5 g of a compound having an ethylhexyl group was obtained.
Similarly, tetrazole derivatives 1 to 12 represented by formula () and tetrazole derivatives 13 to 15 represented by formula () were synthesized by the Mannitz reaction.
【表】【table】
【表】
実施例および比較例
合成例によるテトラゾール誘導体１〜15を鉱油
に添加し、以下に示す銅板腐食試験および酸化試
験により、金属不活性化剤としての性能を評価し
た。その結果を表３に示す。
＜銅板腐食試験＞
動粘度32.5cst（40℃）、粘度指数102の市販タ
ービン油に硫化オレフイン（硫黄濃度40.8％）を
1.0重量添加したものを試料油とし、これにテト
ラゾール誘導体0.01重量％（in）を添加して、
JIS K2513に従つて銅板腐食試験し試験温度100
℃、３時間）を行つた。
＜酸化試験＞
上記の市販タービン油32に、テトラゾール誘導
体0.1重量％（in）を添加して、ASTM D2272に
よる回転式ボンブ酸化試験（試験温度150℃、酸
素圧13Kg/cm2、銅線触媒）を行い、結果を酸素を
18Kg/cm2吸収した時間で評価した。[Table] Examples and Comparative Examples The tetrazole derivatives 1 to 15 according to the synthesis examples were added to mineral oil, and their performance as metal deactivators was evaluated by the copper plate corrosion test and oxidation test shown below. The results are shown in Table 3. <Copper plate corrosion test> Sulfurized olefin (sulfur concentration 40.8%) was added to commercially available turbine oil with a kinematic viscosity of 32.5cst (40℃) and a viscosity index of 102.
The sample oil was prepared by adding 1.0% by weight, and 0.01% by weight (in) of the tetrazole derivative was added to it.
Copper plate corrosion tested according to JIS K2513 at test temperature 100
°C for 3 hours). <Oxidation test> 0.1% by weight (in) of a tetrazole derivative was added to the above commercially available turbine oil 32, and a rotary bomb oxidation test was conducted according to ASTM D2272 (test temperature 150°C, oxygen pressure 13Kg/cm 2 , copper wire catalyst) and oxygenate the result
Evaluation was based on the time taken to absorb 18Kg/ cm2 .
【表】
本発明によるテトラゾール誘導体は、銅板腐食
試験および酸化試験においてすぐれた性能を示
し、またタービン油、作動油など潤滑油として使
用した場合にも好ましい性能を示した。[Table] The tetrazole derivative according to the present invention showed excellent performance in copper plate corrosion tests and oxidation tests, and also showed favorable performance when used as lubricating oils such as turbine oil and hydraulic oil.
Claims (1)
ゾール誘導体から成る金属不活性化剤。 〔ただし、式（）および式（）において、
R1、R2およびR3は同種でも異種でもよく、C1〜
C20アルキル基、C2〜C20アルケニル基、C5〜C12
シクロアルキル基、C6〜C10アリール基、C7〜C9
アラルキル基、あるいはR4O（R5O）oR6〔R4は水
素原子またはC1〜C20アルキル基、R5、R6はC2〜
C3アルキレン基、ｎは０〜４〕で表わされる基
である。〕[Claims] 1 Formula (); and expression (); A metal deactivator comprising at least one tetrazole derivative selected from the group consisting of: [However, in formula () and formula (),
R 1 , R 2 and R 3 may be the same or different, and C 1 to
C20 alkyl group, C2 - C20 alkenyl group, C5 - C12
Cycloalkyl group, C6 - C10 aryl group, C7 - C9
Aralkyl group, or R 4 O (R 5 O) o R 6 [R 4 is a hydrogen atom or a C 1 - C 20 alkyl group, R 5 and R 6 are C 2 -
C 3 alkylene group, n is 0 to 4]. ]
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11039280A JPS5736193A (en) | 1980-08-13 | 1980-08-13 | Metal inactivator and its composition |
| US06/288,343 US4392968A (en) | 1980-08-13 | 1981-07-30 | Metal deactivator and composition containing same |
| GB8124266A GB2082573B (en) | 1980-08-13 | 1981-08-07 | Tetrazole and hydroxyquinoline derivatives useful as metal deactivating agents |
| CH5158/81A CH647768A5 (en) | 1980-08-13 | 1981-08-11 | METAL DEACTIVATOR AND COMPOSITIONS CONTAINING SUCH. |
| DE3131950A DE3131950A1 (en) | 1980-08-13 | 1981-08-12 | Metal deactivator, and composition containing it |
| FR8115695A FR2488615A1 (en) | 1980-08-13 | 1981-08-13 | METAL DEACTIVATOR AND COMPOSITION CONTAINING SAME |
| GB08326141A GB2136797B (en) | 1980-08-13 | 1983-09-29 | Tetrazole derivatives useful as metal deactivators in lubricating oils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11039280A JPS5736193A (en) | 1980-08-13 | 1980-08-13 | Metal inactivator and its composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5736193A JPS5736193A (en) | 1982-02-26 |
| JPS6124438B2 true JPS6124438B2 (en) | 1986-06-11 |
Family
ID=14534640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11039280A Granted JPS5736193A (en) | 1980-08-13 | 1980-08-13 | Metal inactivator and its composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5736193A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62103279A (en) * | 1985-10-30 | 1987-05-13 | 本田技研工業株式会社 | Motorcycle |
| JPS62103280A (en) * | 1985-10-30 | 1987-05-13 | 本田技研工業株式会社 | Motorcycle |
| JP2773121B2 (en) * | 1987-10-15 | 1998-07-09 | スズキ株式会社 | Scooter frame |
| US8357642B2 (en) | 2007-05-24 | 2013-01-22 | Chiyoda Chemical Co., Ltd. | Functional fluid |
-
1980
- 1980-08-13 JP JP11039280A patent/JPS5736193A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5736193A (en) | 1982-02-26 |
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