CN1107470A - Method for preparing benzotriazole aliphatic amine derivative - Google Patents
Method for preparing benzotriazole aliphatic amine derivative Download PDFInfo
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- CN1107470A CN1107470A CN 94112451 CN94112451A CN1107470A CN 1107470 A CN1107470 A CN 1107470A CN 94112451 CN94112451 CN 94112451 CN 94112451 A CN94112451 A CN 94112451A CN 1107470 A CN1107470 A CN 1107470A
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- 239000012964 benzotriazole Substances 0.000 title claims abstract description 14
- -1 benzotriazole aliphatic amine derivative Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000003377 acid catalyst Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- BMOKHTQIBPRXSL-UHFFFAOYSA-N 2h-benzotriazole;sodium Chemical compound [Na].C1=CC=CC2=NNN=C21 BMOKHTQIBPRXSL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 150000008431 aliphatic amides Chemical class 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 5
- 238000001816 cooling Methods 0.000 abstract description 5
- 239000010949 copper Substances 0.000 abstract description 5
- 229910052802 copper Inorganic materials 0.000 abstract description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 21
- 238000012360 testing method Methods 0.000 description 9
- 238000007792 addition Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N N-butyl-butylamine Natural products CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- HLLOAHWFPRCYJY-UHFFFAOYSA-N 2h-benzotriazole;octadecan-1-amine Chemical compound C1=CC=CC2=NNN=C21.CCCCCCCCCCCCCCCCCCN HLLOAHWFPRCYJY-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 241000201295 Euphrasia Species 0.000 description 1
- 229910000806 Latten Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- Lubricants (AREA)
Abstract
The process for preparing aliphatic amine derivative of benzotriazole includes reaction of sodium benzotriazole, aliphatic ammonium or formaldehyde, and aliphatic amine at 70-100 deg.C for 2-6 hr in the presence of acid catalyst; demixing, water washing and drying; or codissolving of coarse product and methanol by heating, cooling for layering, and heating for removing residual methanol. Said derivative has excellent oil-soluble, antirust and antiwear performance, so having better protection of copper.
Description
The invention belongs to preparation method, particularly utilize benzotriazole sodium, aliphatic amide or formaldehyde, aliphatic amide to prepare the method for oil soluble benzotriazole aliphatic amine derivative as the benzotriazole aliphatic amine derivative of oil dope.
Benzotriazole aliphatic amine derivative, because of having oil soluble and good antioxygen, wear-resisting, antirust and metal passivation performance preferably, be added on and be used as rust-preventive agent, oxidation inhibitor, metal passivator, anti-friction composition, sanitas etc. in crude mineral oils, oil fuel and the lubricating oil, obtained good effect.Once had many patents and article to introduce this analog derivative preparation, application and effect abroad, for example GB 1,061, and 904(1967), JP discloses clear 58-25, and 393, US 3,697,427(1972); 3,790,481(1974) all provide the preparation method and the application performance thereof of the multiple derivative of benzotriazole aliphatic amine.Yet the related method of above-mentioned patent is solvent all from benzotriazole, aliphatic amide, formaldehyde with methyl alcohol, or reaction conditions control is strict, or is reflected under the nitrogen protection and carries out, and product yield is lower.
At the described preparation method's of background technology shortcoming, the invention provides a kind of raw material and use rationally, reaction conditions is simple, and reaction is carried out relaxing, and product yield height and quality product be the method for synthetic benzotriazole aliphatic amine derivative better.
The manufacture method that the present invention relates to is: in the presence of an acidic catalyst, by benzotriazole sodium (BTZ-S, down with), aliphatic amide or formaldehyde, aliphatic amide carry out as shown in the formula reaction:
R1=H wherein, CH3; R2 is the aliphatic group of C4～C20.Used acid catalyst can be used organic acid and mineral acid, and the most frequently used is hydrochloric acid, sulfuric acid, acetic acid.Because BTZ-S is water-soluble, acid catalyst is soluble in water, thereby reacts and can carry out in water, and BTZ-S often is made into 15～35% aqueous solution, and acid catalyst is made into 20～80% solution and uses.Temperature of reaction is 70～100 ℃ during material reaction, and the reaction times is 2.0～6.0h.Response procedures is the BTZ-S solution that adds specified amount in reactor, stirs to add aliphatic amide or formaldehyde, aliphatic amide down, is warming up to reaction and requires to drip under the temperature acid catalyst solutions, then reacts with this understanding to the specified time and finishes.The processing of reaction after finishing can first layering, and oil reservoir is washed with water to neutrality, dehydrate then product, be advisable with vacuum-drying; The also crude product that the reactant layering can be obtained and isopyknic methanol mixed, heating for dissolving, and postcooling is told oil reservoir, be heated remove the methyl alcohol that is dissolved in oil reservoir and product.Participating in the reaction raw materials mol ratio is:
Formula (1) aliphatic amide: BTZ-S: acid catalyst=1.0: 1.0～1.2: 1.0～1.2;
Formula (2) (3) aliphatic amide: formaldehyde: BTZ-S: acid catalyst=1.0: 1.0～2.2: 1.0～2.2: 1.0～2.2.
Yield with the inventive method preparing product reaches 70～90%, the purity height of product, and quality is good, be applied to superior performance in the oil product.
The present invention and background technology are relatively; its outstanding feature is: (1) benzotriazole sodium has good water-solubility; thereby be reflected in the water and carry out; do not need organic solvent; do not need nitrogen protection, thereby relaxed processing condition, product yield is higher; reduced cost in the whole process of preparation, also reduced pollution simultaneously environment.(2) make same product relatively with traditional method, be improved at aspects such as oil soluble, rust-preventing characteristic and anti-attritions.
Example 1
The preparation of benzotriazole stearylamine (abbreviation product A)
Benzotriazole sodium water solution 353g with 20% adds in the reactor, stir and add the 134g stearylamine down, heat up, begin to drip 80% acetic acid 37.5g when reaching 80 ℃, dropwise at 80～100 ℃ and react 3h down, it is neutral, cooling layering that reaction finishes with 60～80 ℃ of water washing oil reservoirs, the dehydration of oil reservoir heating under vacuum, get product 174g, yield 90%.
Example 2
N, the preparation of the two benzotriazole dimethylene stearylamines (B) of N-.
Get 20% benzotriazole sodium water solution 353g, add in the reactor, stirring adds stearylamine 67g down, 37% formaldehyde 54g, and heating drips 80% sulfuric acid 24.5g when reaching 90 ℃, react 6h down at 80～100 ℃.The cooling layering is finished in reaction, oil reservoir and equivalent methanol mixed, the layering of heating for dissolving postcooling, oil reservoir add the heat extraction residual solvent, cool off product 105.6g, yield 80%.
Example 3
I-(di-n-butyl amine methylene radical)-preparation of benzotriazole (C).
Get 20% benzotriazole sodium water solution 353g, add in the reactor, stirring adds Di-n-Butyl Amine 64.5g down, 37% formaldehyde solution 54g, and heating drips 80% acetic acid 37.5g when reaching 70 ℃, react 6h down at 70～80 ℃.The cooling layering is finished in reaction, and oil reservoir and equivalent methanol mixed are heated to 50 ℃ of dissolvings, the cooling layering, and oil reservoir adds the residual solvent of heat extraction, gets light yellow liquid product 104g, yield 80%.
Example 4
Product-benzotriazole stearylamine (A) that example 1～3 is made, N, the two benzotriazole dimethylene stearylamines (B) of N-, 1-(Di-n-Butyl Amine methylene radical)-benzotriazole-carry out the full test of performances such as oil soluble, rust-preventing characteristic and wear resistance, its result is as shown in table 1.
Table 1
Sequence number test event product A product B products C testing method
The range estimation of 1 light brown in appearance solid light yellow solid light yellow liquid
2 fusing points ℃ 53 59.5-capillary tube technique
3 oil solubles
25 ℃ of additions
0.5% complete molten transparent complete molten transparent complete molten transparent range estimation
1.0% complete molten transparent complete molten transparent complete molten transparent range estimation
2.0% complete molten transparent complete molten transparent complete molten transparent range estimation
0℃(3h.)
The bright little deep colling of the bright little deep colling of the 1.0% little deep colling side that makes eye bright
100℃(3h.)
1.0% clear transparent clear transparent clear transparent order side
Room temperature 48h.1.0% clear transparent clear transparent clear transparent order side
4 corrosion tests
100 ℃ of 3h, the qualified qualified SY-26 of latten(-tin)
20-77
5 rust-preventing characteristics
49 ℃ of relative humidity 95%
3 days 3 grades of 3 grades of 3 grades of SY-13 of 10# steel disc
74-77
0 grade 0 grade 0 grade of 62# copper sheet 6 days
6 four-ball tests
PB N(kgf) GB-
3142
Addition 0.5% 450 400 390
1.0% 500 430 420
2.0% 610 580 570
Illustrate that above-mentioned test result adds the amount of marking (heavy %) additive samples and records in the 10# transformer oil.
The benzotriazole stearylamine (product A) that example 1 is made with carry out performance by the commercial like product of produced in conventional processes relatively, it the results are shown in Table 2.
Table 2
The commercially available state of the product A series products of valency project example one is translated in the sequence number test
1 light brown in appearance solid light brown solid
2 fusing points ℃ 53 55
3 oil solubles
25 ℃ of additions
0.5% complete molten transparent muddiness
1.0% complete molten transparent muddy layering
2.0% complete molten transparent muddy layering
The bright shape muddiness of freezing of 0 ℃ (3h) 1.0 little deep colling
100 ℃ (3h) 1.0% clear transparent clear transparent
The serious layering of room temperature (48h) 1.0% clear transparent
4 rust-preventing characteristics
49 ℃, relative temperature 95%
Addition 1%
3 grades 4 grades of 10# steel discs 3 days
0 grade 1 grade of 62# copper sheet 6 days
5 salt water rettings
3%Nacl addition 1.0%
3 days rustless 1 day rust of 10# steel disc
0 grade 1 grade of 62# copper sheet 6 days
6 four-ball tests
PB N(kgf)
Addition 1.0% 500 (51) 380 (38.8)
Illustrate: above-mentioned test result adds the amount of marking (heavy %) sample and records in the 10# transformer oil.
It seems that from above measured result three kinds of benzotriazole aliphatic amine derivatives that the present invention makes have good oil soluble, rust-preventing characteristic and anti-attrition, particularly copper and alloy thereof are had protective capacities preferably.
Claims (6)
1, a kind of preparation method of benzotriazole aliphatic amine derivative, it is of the present invention that to be characterized as with benzotriazole sodium (BTZ-S), aliphatic amide or formaldehyde, aliphatic amide be raw material, in the presence of acid catalyst, carry out as shown in the formula reaction:
R1=H wherein, CH3; R2 is the aliphatic group of C4～C20; The material molar ratio of participating in reaction is:
Formula (1) aliphatic amide: BTZ-S: acid catalyst=1.0: 1.0～1.2: 1.0～1.2;
Formula (2) (3) aliphatic amide: formaldehyde: BTZ-S: acid catalyst=1.0: 1.0～2.2: 1.0～2.2: 1.0～2.2; With water is reaction medium, and temperature of reaction is 70～100 ℃, and the reaction times is 2.0～6.0h, and the aftertreatment that reaction is finished is that water is washed till neutrality with oil reservoir, dehydrate then and product.
2, preparation method as claimed in claim 1, it is to add the quantitative BTZ-S aqueous solution in reactor that the present invention is characterized as response procedures, add aliphatic amide or formaldehyde, aliphatic amide under stirring, heating up reaches the aqueous solution that drips acid catalyst under the temperature of reaction, and afterreaction to the specified time finishes.
3, preparation method as claimed in claim 1, of the present invention to be characterized as described acid catalyst be hydrochloric acid, sulfuric acid, acetic acid.
4, preparation method as claimed in claim 1 of the present inventionly is characterized as crude product and the isopyknic methanol mixed that aftertreatment that described reaction finishes can obtain the reactant layering, heating for dissolving, and postcooling is told oil reservoir.Be heated remove the methyl alcohol that is dissolved in oil reservoir and product.
5, preparation method as claimed in claim 2 of the present inventionly is characterized as 15～35% the aqueous solution that the described BTZ-S aqueous solution is the BTZ-S that is mixed with.
6, preparation method as claimed in claim 2, the aqueous solution that is characterized as described acid catalyst of the present invention is 20～80% the aqueous solution that is mixed with acid catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94112451 CN1107470A (en) | 1994-08-19 | 1994-08-19 | Method for preparing benzotriazole aliphatic amine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94112451 CN1107470A (en) | 1994-08-19 | 1994-08-19 | Method for preparing benzotriazole aliphatic amine derivative |
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| CN1107470A true CN1107470A (en) | 1995-08-30 |
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| CN 94112451 Pending CN1107470A (en) | 1994-08-19 | 1994-08-19 | Method for preparing benzotriazole aliphatic amine derivative |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308487C (en) * | 2002-05-01 | 2007-04-04 | 大塚化学株式会社 | Anti-rust agent and anti-rust method using it |
| CN104649985A (en) * | 2013-11-25 | 2015-05-27 | 刘现梅 | Water-soluble methylene derivative of methylbenzotriazole and preparation method thereof |
| CN107312036A (en) * | 2016-04-27 | 2017-11-03 | 中国石油化工股份有限公司 | A kind of benzotriazole derivatives, its manufacture method and its application |
| CN107522670A (en) * | 2017-06-05 | 2017-12-29 | 东莞理工学院 | A kind of alkylacetamidobenzotriazole derivative lubricating oil additive and preparation method thereof |
| CN107922870A (en) * | 2015-08-14 | 2018-04-17 | 范德比尔特化学品有限责任公司 | Lubricant composition additives comprising sulfur-containing and sulfur-free organomolybdenum compounds and triazoles |
| CN109023380A (en) * | 2017-06-08 | 2018-12-18 | 滨州学院 | A kind of compound corrosion inhibitor and preparation method thereof of the B30 corronil suitable for Seawater |
| CN109023383A (en) * | 2017-06-08 | 2018-12-18 | 滨州学院 | A kind of compound corrosion inhibitor and preparation method thereof of the B10 corronil suitable for Seawater |
| CN109208004A (en) * | 2017-07-04 | 2019-01-15 | 滨州学院 | It is a kind of suitable for AZ91D magnesium alloy strong acid corrosive medium composite corrosion inhibitor and preparation method thereof |
| CN109208005A (en) * | 2017-07-04 | 2019-01-15 | 滨州学院 | A kind of pre- film corrosion inhibiter of the B30 corronil suitable for Seawater and preparation method thereof |
| CN109748879A (en) * | 2019-02-28 | 2019-05-14 | 盘锦辽河油田大力集团有限公司 | A kind of modified benzotriazole and preparation method thereof |
| CN109750295A (en) * | 2017-11-06 | 2019-05-14 | 滨州学院 | A kind of compound corrosion inhibitor suitable for aluminum alloy in strong acid corrosion medium and preparation method thereof |
| CN110256366A (en) * | 2019-07-01 | 2019-09-20 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of benzotriazole derivative |
| CN111471029A (en) * | 2020-05-06 | 2020-07-31 | 滨州市坤厚工贸有限责任公司 | Liquid multi-effect lubricating oil oily agent and preparation method thereof |
| CN111732551A (en) * | 2020-07-07 | 2020-10-02 | 新乡市瑞丰新材料股份有限公司 | Preparation method of novel N, N-di-N-butylaminobenzotriazole |
-
1994
- 1994-08-19 CN CN 94112451 patent/CN1107470A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308487C (en) * | 2002-05-01 | 2007-04-04 | 大塚化学株式会社 | Anti-rust agent and anti-rust method using it |
| CN104649985A (en) * | 2013-11-25 | 2015-05-27 | 刘现梅 | Water-soluble methylene derivative of methylbenzotriazole and preparation method thereof |
| CN107922870A (en) * | 2015-08-14 | 2018-04-17 | 范德比尔特化学品有限责任公司 | Lubricant composition additives comprising sulfur-containing and sulfur-free organomolybdenum compounds and triazoles |
| CN107312036A (en) * | 2016-04-27 | 2017-11-03 | 中国石油化工股份有限公司 | A kind of benzotriazole derivatives, its manufacture method and its application |
| CN107522670A (en) * | 2017-06-05 | 2017-12-29 | 东莞理工学院 | A kind of alkylacetamidobenzotriazole derivative lubricating oil additive and preparation method thereof |
| CN109023383A (en) * | 2017-06-08 | 2018-12-18 | 滨州学院 | A kind of compound corrosion inhibitor and preparation method thereof of the B10 corronil suitable for Seawater |
| CN109023380A (en) * | 2017-06-08 | 2018-12-18 | 滨州学院 | A kind of compound corrosion inhibitor and preparation method thereof of the B30 corronil suitable for Seawater |
| CN109208004A (en) * | 2017-07-04 | 2019-01-15 | 滨州学院 | It is a kind of suitable for AZ91D magnesium alloy strong acid corrosive medium composite corrosion inhibitor and preparation method thereof |
| CN109208005A (en) * | 2017-07-04 | 2019-01-15 | 滨州学院 | A kind of pre- film corrosion inhibiter of the B30 corronil suitable for Seawater and preparation method thereof |
| CN109750295A (en) * | 2017-11-06 | 2019-05-14 | 滨州学院 | A kind of compound corrosion inhibitor suitable for aluminum alloy in strong acid corrosion medium and preparation method thereof |
| CN109748879A (en) * | 2019-02-28 | 2019-05-14 | 盘锦辽河油田大力集团有限公司 | A kind of modified benzotriazole and preparation method thereof |
| CN110256366A (en) * | 2019-07-01 | 2019-09-20 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of benzotriazole derivative |
| CN111471029A (en) * | 2020-05-06 | 2020-07-31 | 滨州市坤厚工贸有限责任公司 | Liquid multi-effect lubricating oil oily agent and preparation method thereof |
| CN111471029B (en) * | 2020-05-06 | 2023-03-10 | 滨州市坤厚工贸有限责任公司 | Liquid multi-effect lubricating oil oiliness agent and preparation method thereof |
| CN111732551A (en) * | 2020-07-07 | 2020-10-02 | 新乡市瑞丰新材料股份有限公司 | Preparation method of novel N, N-di-N-butylaminobenzotriazole |
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