JPH02207077A - Benzotriazole derivative - Google Patents
Benzotriazole derivativeInfo
- Publication number
- JPH02207077A JPH02207077A JP2586789A JP2586789A JPH02207077A JP H02207077 A JPH02207077 A JP H02207077A JP 2586789 A JP2586789 A JP 2586789A JP 2586789 A JP2586789 A JP 2586789A JP H02207077 A JPH02207077 A JP H02207077A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- benzotriazole
- expressed
- maleic anhydride
- benzotriazole derivative
- 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.)
- Pending
Links
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 title claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052802 copper Inorganic materials 0.000 abstract description 9
- 239000010949 copper Substances 0.000 abstract description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 9
- 239000012964 benzotriazole Substances 0.000 abstract description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004677 Nylon Substances 0.000 abstract description 4
- 229920001778 nylon Polymers 0.000 abstract description 4
- 230000003449 preventive effect Effects 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 2
- -1 benzotriazole compound Chemical class 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 238000007259 addition reaction Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000001565 benzotriazoles Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野］
本発明は、新規なベンゾトリアゾール誘導体に関する０
本発明に係るベンゾトリアゾール誘導体は、銅に対する
防錆剤として有用であるとともに、ナイロン、ポリエス
テル等の樹脂原料等として有用である。Detailed Description of the Invention [Industrial Application Field] The present invention relates to novel benzotriazole derivatives.
The benzotriazole derivative according to the present invention is useful as a rust preventive agent for copper, and is also useful as a raw material for resins such as nylon and polyester.
〔従来の技術および発明が解決しようとする課題〕従来
、ベンゾトリアゾール誘導体が金属に対する防錆作用を
有することは知られている。本発明は、防錆効果に優れ
た新規なベンゾトリアゾールを提供する。また、従来、
ナイロン等には、強化剤として銅（コラ化銅）が添加さ
れているが、そのため加工時に熱履歴によって着色する
等の問題がある。本発明のベンゾトリアゾール誘導体は
、ナイロン分子の骨格に取り込むことができ、銅を保護
するとともに着色を防止する等の効果を与える。[Prior Art and Problems to be Solved by the Invention] It has been known that benzotriazole derivatives have a rust-preventing effect on metals. The present invention provides a novel benzotriazole with excellent antirust effect. Also, conventionally,
Copper (copper cola) is added to nylon as a reinforcing agent, but this causes problems such as coloring due to heat history during processing. The benzotriazole derivative of the present invention can be incorporated into the skeleton of a nylon molecule, and provides effects such as protecting copper and preventing discoloration.
本発明は、下記式で示されるベンゾトリアゾール誘導体
を提供する。The present invention provides a benzotriazole derivative represented by the following formula.
ＣＨＣＯＲｔ
ＣＨＩＣＯＲｆｆｉ
上式中、Ｒ１は水素原子またはメチル基を表し、Ｒ２お
よびＲ１はそれぞれ−ＯＨを表すかまたは両者がいっし
ょになって：；Ｏを表す。CHCORt CHICORffi In the above formula, R1 represents a hydrogen atom or a methyl group, and R2 and R1 each represent -OH or both represent :;O.
これらの誘導体は、下記式、
〔上式中、Ｒ１は前記規定に同一のものを表す〕で示さ
れるベンゾトリアゾールの無水マレイン酸付加物を得、
所望によりこれを加水分解して、下記式、
■
〔上式中、Ｒ，は前記規定に同一のものを表す〕で示さ
れるベンゾトリアゾール化合物を無水マレイン酸と付加
反応させることにより、下記式、ＣＨＣ００１１
ＣｌｌＣＯＯ■
〔上式中、Ｒ８は前記規定に同一のものを表す］で示さ
れるジカルボン酸を得ることにより、製造することがで
きる。These derivatives obtain maleic anhydride adducts of benzotriazole represented by the following formula: [In the above formula, R1 represents the same thing as defined above],
If desired, this is hydrolyzed and a benzotriazole compound represented by the following formula: It can be produced by obtaining a dicarboxylic acid represented by CHC0011 CllCOO■ [In the above formula, R8 represents the same thing as defined above].
さらに詳細には、例えば、ベンゾトリアゾールまたはト
リルトリアゾールと無水マレイン酸の等モル量を、適当
な溶剤の存在下に常圧において、５０〜１００℃の温度
で４〜６時間反応させる０次に、所望により、この反応
混合物に、１〜１．２倍モル量の水を満願し、８０〜９
０℃の温度で１〜２時間加水分解を行う。反応溶剤とし
ては、ベンゼン、トルエン、キシレン等の芳香族炭化水
素類を好ましく用いることができるけれども、これらに
限定されるものではない。More specifically, for example, equimolar amounts of benzotriazole or tolyltriazole and maleic anhydride are reacted in the presence of a suitable solvent at normal pressure at a temperature of 50 to 100° C. for 4 to 6 hours. If desired, 1 to 1.2 times the molar amount of water is added to the reaction mixture to give 80 to 9 molar amounts of water.
Hydrolysis is carried out for 1-2 hours at a temperature of 0°C. As the reaction solvent, aromatic hydrocarbons such as benzene, toluene, and xylene can be preferably used, but the reaction solvent is not limited thereto.
反応終了後氷冷し、析出した結晶またはオイル状物質を
濾過または分離し、乾燥すれば高収率で目的物が得られ
る。特に必要が有れば、水、水メタノール、水−アセト
ン溶媒で洗浄または再結晶し、精製することができる。After the reaction is completed, the desired product can be obtained in high yield by cooling with ice, filtering or separating the precipitated crystals or oily substance, and drying. If particularly necessary, it can be purified by washing or recrystallizing with water, water-methanol, or water-acetone solvent.
〔実施例］ 以下、実施例により、本発明をさらに説明する。〔Example] The present invention will be further explained below with reference to Examples.
実施例１
撹拌機、温度計および還流器を備えた四ロフラスコに１
．２．３−ベンゾトリアゾール５０ｇ（０，４２モル）
、無水マレイン酸４２ｇ（０，４３モル）およびトルエ
ン４００ｃｃを仕込み、７０〜８０°Ｃにて４時間反応
を継続する０反応液は無色透明から褐色に変化し、結晶
が析出する。Example 1 In a four-hole flask equipped with a stirrer, thermometer and reflux, 1
．． 2.3-benzotriazole 50g (0.42 mol)
, 42 g (0.43 mol) of maleic anhydride, and 400 cc of toluene were charged, and the reaction was continued at 70 to 80° C. for 4 hours. The reaction solution turned from colorless and transparent to brown, and crystals precipitated.
得られた結晶を濾別し、乾燥して、下記式の化合物を得
る。The obtained crystals are filtered and dried to obtain a compound of the following formula.
融点；１５５〜１６０°Ｃ
ＩＲ分析
１６２０〜１６８０Ｃ１１−’の−Ｃ＝Ｃ−伸縮振動お
よび１６２０ｃｍ−’の−ＮＨ吸収の何れも消滅し、ｌ
、２゜３−ベンゾトリアゾールの無水マレイン酸付加物
であることが確認された。Melting point: 155-160°C IR analysis Both the -C=C- stretching vibration of 1620-1680C11-' and the -NH absorption of 1620 cm-' disappear, and l
, was confirmed to be a maleic anhydride adduct of 2°3-benzotriazole.
実施例２
実施例１の操作を繰り返して得られた、結晶が析出した
反応混合物に、次いで水８ｇ（０，４４モル）を滴下し
、８０〜９０°Ｃにて１時間加水分解反応を継続した後
、水冷後、結晶をろ過し、乾燥すると、９０ｇの１．２
．３−ベンゾトリアゾール誘導体を得る。得率は９１％
であった。Example 2 8 g (0.44 mol) of water was then added dropwise to the reaction mixture in which crystals had precipitated, obtained by repeating the operation of Example 1, and the hydrolysis reaction was continued at 80 to 90 °C for 1 hour. After cooling with water, the crystals are filtered and dried to give 90g of 1.2
．． A 3-benzotriazole derivative is obtained. Gain rate is 91%
Met.
更に水溶媒中にて再結晶すると融点１９０〜１９２°Ｃ
１酸価４７０■ＫＯＩＩ／ｇ（計算値；４７７Ｉ１ｇＫ
ＯＨ／ｇ）の高純度ベンゾトリアゾール誘導体を得た。Furthermore, when recrystallized in an aqueous solvent, the melting point is 190-192°C.
1 acid value 470■KOII/g (calculated value; 477I1gK
A high purity benzotriazole derivative of OH/g) was obtained.
元素分析結果
−ＮＨ吸収が消滅し、目的の１．２．３−ベンゾトリア
ゾール誘導体が確認された。Elemental analysis results - NH absorption disappeared and the desired 1,2,3-benzotriazole derivative was confirmed.
実施例３
攪拌機、温度計および還流器を備えた四ロフラスコにト
リルトリアゾール５６ｇ（０，４２モル）、無水マレイ
ン酸４２ ｇ （０，４３モル）およびトルエン４００
ｃｃを仕込み、７０〜８０’Ｃにて５時間反応を継続す
る。反応液は黄色から茶褐色に変化する。Example 3 56 g (0.42 mol) of tolyltriazole, 42 g (0.43 mol) of maleic anhydride and 400 g of toluene are placed in a four-hole flask equipped with a stirrer, thermometer and reflux.
cc and continue the reaction at 70-80'C for 5 hours. The reaction solution changes from yellow to brown.
減圧下、トルエンを留去することにより、下記の化合物
を得る。The following compound is obtained by distilling off toluene under reduced pressure.
各元素共に計算値と良く一致した
更にＩＲ（赤外分光光度計）分析の結果、１７００Ｏ
ｃｍ”’に−Ｃ−ＯＨの−Ｃ＝Ｏ伸縮振動、２５００ｃ
ｍ−’に−ＯＨ伸縮振動が強く表れ、更に１（ｉ２０ｃ
ｍ−’の融点；６０〜７０°Ｃ
ＩＲ分析
１６２０〜１６８０ｃｍ−’の−Ｃ＝Ｃ−伸縮振動及び
１６２０ｃ＋ａ−’の−ＮＨ吸収の何れも消滅し、トリ
ルトリアゾールの無水マレイン酸付加物であることが確
認された。Furthermore, as a result of IR (infrared spectrophotometer) analysis, which was in good agreement with the calculated values for each element, -C=O stretching vibration of -C-OH at 1700O cm"', 2500c
-OH stretching vibration appears strongly in m-', and further 1 (i20c
Melting point of m-': 60-70°C IR analysis Both the -C=C- stretching vibration of 1620-1680 cm-' and the -NH absorption of 1620c+a-' disappear, indicating that it is a maleic anhydride adduct of tolyltriazole. This was confirmed.
実施例４
実施例３の操作を繰り返して得られた反応混合物に、次
いで水８ ｇ （０，４４ｍｏｌ）を８０〜９０°Ｃで
滴下すると、オイル状物質が析出する。８０〜９０°Ｃ
にて１、５時間加水分解を継続した後、２０°Ｃに冷却
し、オイル物質をトルエンより分離して加熱真空乾燥す
ると、９７ｇのトリルトリアゾール誘導体を得る。得率
は９３％であった。Example 4 When 8 g (0.44 mol) of water is then added dropwise to the reaction mixture obtained by repeating the operation of Example 3 at 80-90°C, an oily substance is precipitated. 80~90°C
After continuing hydrolysis for 1.5 hours at 20°C, the mixture was cooled to 20°C, and the oil substance was separated from toluene and dried under heat under vacuum to obtain 97g of tolyltriazole derivative. The yield rate was 93%.
更に水−メタノール混合溶媒で洗浄を繰返し、精製する
と、融点９５〜９８°Ｃ１酸価４４０■にＯＨ／ｇ（計
算値；４５０［Ｉ１ｇＫＯＨ／ｇ）の高純度トリルトリ
アゾール誘導体を得る。Further washing with a mixed solvent of water and methanol is repeated for purification to obtain a highly pure tolyltriazole derivative with a melting point of 95 to 98 DEG C., an acid value of 440 OH/g (calculated value: 450 [I1 gKOH/g)].
元素分析結果 各元素共に計算値と良く一致した。Elemental analysis results The calculated values for each element agreed well.
−Ｃ＝０伸縮振動、２５００Ｃ１１−’に−ＯＨ伸縮振
動の吸収ピークが表れ、１６２０ＣＩｍ−’の−ＮＨ吸
収が消滅し、目的のトリルトリアゾール誘導体が確認さ
れた。-C=0 stretching vibration, absorption peak of -OH stretching vibration appeared at 2500C11-', -NH absorption of 1620CIm-' disappeared, and the target tolyltriazole derivative was confirmed.
銅に・する方ｔテスト
■ ＪＩＳ−に２５１３石油製品銅板腐食試験方法によ
り防錆テストを行なった。Test for Copper■ A rust prevention test was conducted according to the JIS-2513 Petroleum Products Copper Plate Corrosion Test Method.
条件： １００″Ｃ／３時間
配合；ベースオイル（モンサント基油） ９６部腐食
促進剤（ＤＡＩＬＵＢＵ Ｓ−３８５、大日本インキ化
学工業■製） ４部
防錆剤（実施例１または３の化合物）０．１部テスト結
果：
（へＳＴＭ銅板腐食標準）
ブランク ：４ｂ
防錆剤添加＝２ａ
実施例１および実施例３の化合物ともに銅に対して良好
な防錆効果を示した。Conditions: 100″C/3 hours blending; Base oil (Monsanto base oil) 96 parts Corrosion accelerator (DAILUBU S-385, manufactured by Dainippon Ink & Chemicals) 4 parts Rust inhibitor (compound of Example 1 or 3) 0 . Part 1 test results: (STM copper plate corrosion standard) Blank: 4b Addition of rust preventive agent = 2a Both the compounds of Example 1 and Example 3 showed a good rust preventive effect on copper.
■ ５％食塩水２００ｄ中に実施例２または４のベンゾ
トリアゾール誘導体０．１ ｇを溶解し、この溶液中に
銅線を浸し、５０″Ｃのインキュベーター中に放置する
。(2) Dissolve 0.1 g of the benzotriazole derivative of Example 2 or 4 in 200 d of 5% saline, immerse the copper wire in this solution, and leave it in an incubator at 50''C.
★；表面が茶褐色に変化し、緑錆が発生して溶液が不透
明になる。★: The surface turns brown, green rust occurs, and the solution becomes opaque.
ム：表面全体が薄褐色に変化する。Mu: The entire surface turns light brown.
０２表面の一部に黒錆が発する。02 Black rust appears on a part of the surface.
◎：裏表面ほとんど変化が見られない。◎: Almost no change is observed on the back surface.
実施例２及び４の化合物ともに食塩水中において銅に対
して良好な防錆効果を示す。Both the compounds of Examples 2 and 4 exhibit good antirust effects on copper in saline.
Claims (1)
２およびＲ＿３はそれぞれ−ＯＨを表すかまたは両者が
いっしょになって▲数式、化学式、表等があります▼を
表す。[Claims] 1. A benzotriazole derivative represented by the following formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the above formula, R_1 represents a hydrogen atom or a methyl group, and R_
2 and R_3 each represent -OH, or both together represent ▲There are mathematical formulas, chemical formulas, tables, etc.▼.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2586789A JPH02207077A (en) | 1989-02-06 | 1989-02-06 | Benzotriazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2586789A JPH02207077A (en) | 1989-02-06 | 1989-02-06 | Benzotriazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02207077A true JPH02207077A (en) | 1990-08-16 |
Family
ID=12177745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2586789A Pending JPH02207077A (en) | 1989-02-06 | 1989-02-06 | Benzotriazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02207077A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005539094A (en) * | 2001-12-20 | 2005-12-22 | コグニテク マネージメント システムズ インコーポレイテッド | Composition for increasing thermal conductivity of heat transfer medium and method of use thereof |
| CN115850196A (en) * | 2022-11-29 | 2023-03-28 | 河北宝力工程装备股份有限公司 | Non-phosphorus multifunctional high-efficiency corrosion inhibitor and preparation method thereof |
-
1989
- 1989-02-06 JP JP2586789A patent/JPH02207077A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005539094A (en) * | 2001-12-20 | 2005-12-22 | コグニテク マネージメント システムズ インコーポレイテッド | Composition for increasing thermal conductivity of heat transfer medium and method of use thereof |
| CN115850196A (en) * | 2022-11-29 | 2023-03-28 | 河北宝力工程装备股份有限公司 | Non-phosphorus multifunctional high-efficiency corrosion inhibitor and preparation method thereof |
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