WO2013026251A1 - 曼尼希碱脱钙缓蚀剂及其制备和应用 - Google Patents
曼尼希碱脱钙缓蚀剂及其制备和应用 Download PDFInfo
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- WO2013026251A1 WO2013026251A1 PCT/CN2012/000566 CN2012000566W WO2013026251A1 WO 2013026251 A1 WO2013026251 A1 WO 2013026251A1 CN 2012000566 W CN2012000566 W CN 2012000566W WO 2013026251 A1 WO2013026251 A1 WO 2013026251A1
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- Prior art keywords
- mannich base
- inhibitor
- decalcification
- corrosion
- acid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
- C10G75/02—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of corrosion inhibitors
-
- 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
-
- 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
- C23F11/141—Amines; Quaternary ammonium compounds
-
- 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
Definitions
- the invention relates to a Mannich base decalcification inhibitor and its preparation and application.
- CN 1224078A, CN 1231347A respectively describe a corrosion inhibitor which can only inhibit the corrosion of steel in simple brine;
- CN 1388271A describes a steel for the high temperature acidic medium (below 16CTC for 20% hydrochloric acid or earth acid) Etchant and preparation method thereof.
- ZL200610112532X introduces a corrosion inhibitor which can be used in the desalting and dehydration unit salt, acid and water mixed medium of refinery crude oil and its preparation method, which is composed of 10 ⁇ 99.5% (wt%) of main corrosion inhibitor and balance
- the auxiliary corrosion inhibitor is a combination of two components.
- the main corrosion inhibitor is a high temperature organic acid corrosion inhibitor synthesized by using boric acid and organic amine
- the auxiliary corrosion inhibitor is a ketone aldehyde amine corrosion inhibitor, an imidazoline corrosion inhibitor, an alkyne oxymethylamine corrosion inhibitor, etc.
- One or more of the commercially available corrosion inhibitors are combined.
- Duan Xiaoyun Li Pengjiang used formaldehyde, cyclohexylamine and acetophenone as main raw materials to synthesize Mannich base corrosion inhibitors by Mannich reaction, and studied the synthesis of Mannich bases by formaldehyde, cyclohexylamine and acetophenone. Effect of Corrosion Inhibition Performance [Section Xiaoyun, Li Pengjiang. A Study on Synthesis of Mannich Base Corrosion Inhibitor. Chemical Technology and Development.
- Chinese patent CN 100577877C discloses a method for synthesizing Mannich base steel corrosion inhibitor mother liquor and a steel corrosion inhibitor mother liquor, which is passed through a secondary amine, an aldehyde and a mercapto group, a cycloalkyl group, an aromatic group or a halogen in an aqueous medium.
- CN 101451242 A "High temperature acidification inhibitor for Cr-containing oil pipes” discloses an acid corrosion inhibitor,
- the composition of the main agent A is: 25 parts to 35 parts of quinoline quaternary ammonium salt or quinoline derivative quaternary ammonium salt, 5 parts to 10 parts of potassium iodide and 40 parts to 60 parts of organic solvent methanol or formaldehyde.
- the composition of the auxiliary B is: 30 parts to 50 parts of Mannich base, 15 parts to 35 parts of propynyl alcohol, 5 parts to 15 parts of chromium chloride and 20 parts to 35 parts of formaldehyde.
- a Mannich base type curing agent which synthesizes an epoxy system or a polyurethane system with a phenol compound, formaldehyde and at least one polyamine, in order to make the phenol compound as complete as possible The reaction does not leave, resulting in poor environmental friendliness of the product, and an excess of amine is used in the patent; the patent disclosed in CN 101182296A also reports a curing agent for epoxy or polyurethane systems based on dicyclohexanone, formaldehyde and At least one polyamine is synthesized by a Mannich reaction, and an amine ratio excess is also employed.
- a Mannich type corrosion inhibitor ie, a ketone aldehyde amine corrosion inhibitor
- a Mannich type corrosion inhibitor has a ketone, an aldehyde, an amine (monoamine) in a ratio of 1:1:1 or a ketone, an aldehyde, an amine (diamine).
- the ratio is 2:2:1. Therefore, the obtained Mannich base is a linear structure, and its adsorption center is distributed at one end or both ends of the molecule.
- the linear Mannich type corrosion inhibitor meets the metal wall surface, it is expressed as a side.
- the object of the present invention is to provide a Mannich base decalcification inhibitor, which is a decalcification retardation of a multi-branched space-shaped Mannich base or a chiral Mannich base corrosion inhibitor component.
- the amine or secondary amine group is subjected to Mannich reaction with a ketone or an aldehyde, respectively, that is, a functional group grafting on a plurality of amine groups is sufficiently utilized by an organic polyamine to obtain a multi-branched Mannich base corrosion inhibitor structure.
- Another object of the present invention is to provide a method for preparing a Mannich base decalcification inhibitor, which is a Mannich base corrosion inhibition group comprising 10 to 80% of the total weight of the Mannich base decalcification inhibitor.
- a Mannich base decalcification inhibitor which is a Mannich base corrosion inhibition group comprising 10 to 80% of the total weight of the Mannich base decalcification inhibitor.
- One or more components of the imidazoline or alkynyloxymethylamine corrosion inhibitor are combined.
- the preparation process is simple, the reaction conditions are mild, and the energy consumption is small.
- Mannich base decalcification inhibitor which is prepared by the following steps: 1 Preparation of Mannich base corrosion inhibition component: 3 to 7 moles of ketone, 3 ⁇ 7 moles of aldehyde is added to the reaction vessel, the pH is adjusted to 2 ⁇ 6 with acid, the temperature is controlled at 20-50 ° C, and stirred for 20-30 minutes; under stirring, the 1 mole of organic polyamine and organic solvent are stirred. Adding to the reaction kettle, or adding the pH-adjusted ketone, aldehyde and organic solvent to the organic polyamine, controlling the temperature at 60-90 ° C, the reaction time is 1-3 hours, after the reaction is completed, the system is under nitrogen protection.
- the ketone is one or a combination of two or more of an aliphatic ketone, an alicyclic ketone, and an aromatic ketone.
- the cyclohexanone in the alicyclic ketone includes cyclohexanone, cyclopentanone, cycloheptanone, o-methylcyclohexanone, p-methylcyclohexanone, 2-methylcyclopentanone, 2-ethylcyclopentanone , 3-ethylcyclopentanone; fatty ketones, aromatic ketones and other alicyclic ketones can be expressed as:
- 1 2 each independently represent a d-c 6 alkyl group, a C 6 -C 9 linear or branched aromatic group, and a C 5 -C 9 linear or branched cyclic fluorenyl group.
- the aldehyde is formaldehyde or a compound polyoxymethylene which is capable of dissociating formaldehyde, preferably formaldehyde.
- the organic polyamine is an organic compound containing three or more primary and/or secondary amine groups, and is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptaamine. One or more of the components are combined.
- the imidazoline corrosion inhibitor has a molecular weight of from 10 to 750.
- the alkynyloxyamine corrosion inhibitor is alkynyloxymethylamine, alkynyloxymethylbenzylammonium chloride, isopropyldipropynyloxymethylamine, butyldipropynyloxymethylamine, ring Ethyldipropynyloxymethylamine, n-hexyldipropynyloxymethylamine, octyldipropynyloxymethylamine,decyldipropynyloxymethylamine,dodecyldipropynyloxy One or a combination of two or more components of a group amine, tetradecyldipropynyloxymethylamine.
- the raw material may be added by adding an organic polyamine to the ketone or the aldehyde, or by adding a ketone or an aldehyde to the organic polyamine, but the preferred method is to ketone.
- An organic polyamine is added to the aldehyde.
- the reaction is carried out by adding an organic solvent in methanol, ethanol or petroleum ether, preferably the solvent is ethanol; and the acid used in the process of adjusting the pH is one of hydrochloric acid, formic acid and acetic acid, preferably hydrochloric acid.
- Another technical solution provided by the present invention is to provide a method for using a Mannich base decalcification inhibitor, which comprises adding 30 to 2000 ⁇ ⁇ / ⁇ (relative to a corrosive medium) to the corrosive medium and uniformly mixing the corrosion inhibitor.
- the corrosive medium is an aqueous solution of a water-soluble acid corrosive medium containing a water-soluble inorganic salt, in particular, a desalting crude oil of a refinery below 160 ⁇ , a salt, an acid, and a water mixed medium.
- the corrosive medium is: a mixed aqueous solution of a water-soluble inorganic salt and a water-soluble acid.
- the water-soluble inorganic salt is one or more components of a soluble potassium salt, a sodium salt or a magnesium salt;
- the water-soluble acid is a water-soluble inorganic acid and a water-soluble organic acid, and may be hydrochloric acid, hydrofluoric acid, formic acid or acetic acid.
- propionic acid and acetic anhydride is a mixed aqueous solution of a water-soluble inorganic salt and a water-soluble acid.
- composition of the following Mannich base corrosion-inhibiting component and the auxiliary corrosion-inhibiting component is based on the total weight of the Mannich base decalcification inhibitor.
- the structural formula is 40% based on the total weight of the Mannich base decalcification inhibitor. An average molecular weight of 340, and the total weight percent of Mannich base decalcification inhibitor
- Mannich base decalcification inhibitor 30% of the total weight percent of Mannich base decalcification inhibitor is n- ⁇ k cyclopentanoic acid imidazoline corrosion inhibitor with an average molecular weight of 310, and Mannich base decalcification inhibitor
- the total weight percentage is 20% of acetylene methyl benzyl ammonium chloride, 20% tetradecyl dipropyne oxymethylamine corrosion inhibitor according to the total weight percentage of Mannich base decalcification inhibitor Combination, blending time 3h.
- the total weight percentage of decalcification inhibitor is the total weight percentage of decalcification inhibitor.
- the oleic acid imidazoline corrosion inhibitor and 10% isopropyldipropynyloxymethylamine inhibitor as a total weight percentage of Mannich base decalcification inhibitor were blended for 1.5 h.
- a naphthenic acid imidazoline corrosion inhibitor having an average molecular weight of 750 and 25% of butyl dipropynyloxymethylamine based on the total weight of the Mannich base decalcification inhibitor, decalcified by Mannich base
- the total weight percent of corrosion inhibitor is 25% of the decatilyldipropyne oxymethylamine corrosion inhibitor blending time, blending time 2.5h.
- the structural formula of 10% of the total weight of the etchant is ⁇ 2 of the benzoic acid imidazoline slow decalcification inhibitor as a total weight percentage of 15% of the structural formula is
- the cyclopentanoic acid imidazoline corrosion inhibitor with an average molecular weight of 310 was blended for 3 hours.
- the system was heated to 11 (TC, under nitrogen protection, and the reaction water was removed to obtain a Mannich base corrosion-inhibiting component; After the temperature of the Mannich base corrosion inhibitor of 70% of the total weight of the Mannich base decalcification inhibitor is lowered to 50 , the decalcification inhibition by Mannich base is added under normal pressure with stirring.
- the total weight percentage of the agent is 10% of cycloethyldipropynyloxymethylamine and 20% of the total weight percent of the Mannich base decalcification inhibitor is dodecyldipropynyloxymethylamine.
- the etchant was blended and the blending time was 2 h.
- the total weight percentage of cadaveric Mannich base decalcification inhibitor was 20% of the dimethylacetic acid imidazoline corrosion inhibitor of the formula H 2 C—CH 2 H , and the blending time was lh.
- Corrosion inhibitor (Example 1): 10% Mannich base corrosion inhibitor + 9 ⁇ % auxiliary corrosion inhibitor;
- Corrosion inhibitor (Example 5): 50% primary corrosion inhibitor + 50% auxiliary corrosion inhibitor;
- Example 24 125 300 99. 5S 0. 37
- Example 25 130 500 99. 50 0. 62
- Example 26 130 800 99. 63 0. 45
- Example 27 140 1000 99. 56 0. 62
- Example 28 140 1200 99 62 0. 52
- Example 29 150 1500 99. 52 0. 71
- Example 30 160 1700 99. 49 0. 79
- Example 31 160 2000 99. 19 1.
- Corrosion inhibitor (Example 10): 80% primary corrosion inhibitor + 20% auxiliary corrosion inhibitor;
- Corrosion material 16MnR
- the corrosion rate of the 16MnR material can reach 90% or more.
- Example 42 20 80 1 2000 93. 25 9. 51 Example 43 10 60 30 1 00 93. 77 8. 70 Example 44 15 50 35 1000 94. 82 8. 1 1 Example 45 5 30 65 700 94. 97 6. 63 Example 46 3 10 87 600 96. 03 5. 84 Example 47 2 5 93 400 99. 10 0. 82 Example 48 1 2. 5 96. 5 200 93. 18 4. 73 Example 49 0. 5 1. 0 98. 5 100 92. 56 3. 60 Example 50 0. 1 0. 5 99. 4 80 92. 23 3. 22 Example 51 1 10 90 50 87. 45 4. 14 Example 52 5 1 95 30 92. 10 0. 97 Examples 42 to 52 show: Corrosion inhibition rate of 16MnR for 30 ⁇ 200 ( ⁇ g/g Mannich base decalcification inhibitor) in corrosive media with different concentrations Both can reach more than 90%.
- the present invention adopts the above technical solutions, and has the following advantages compared with the prior art:
- the corrosion inhibitor prepared by the invention adopts an organic polyamine containing three or more primary amino groups and/or secondary amine groups as an amine component of the main ingredient reaction raw material, and the organic polyamine is added to the excess ketone and aldehyde by adding the organic polyamine.
- At least three primary and/or secondary amine groups on the organic polyamine are subjected to a Mannich reaction in a ketone or an aldehyde, and the organic polyamine is used to carry out functional group grafting on a plurality of amine groups to obtain a plurality of
- the Mannich base corrosion inhibitor of the branched space shape increases the adsorption center of the obtained product, and can form multi-point adsorption with the metal surface, and the formed adsorption film is firm and has strong adsorption force.
- the molecular shape of the space shape Mannich base corrosion inhibitor is larger than that of the prior art linear Mannich base.
- the Mannich base decalcification inhibitor prepared by using the main agent overcomes the disadvantages of the prior art that the corrosion inhibitor has few adsorption centers, a single adsorption group, and a weak adsorption force with the metal surface.
- the decalcification inhibitor can It is effectively compounded with crude oil demulsifier and crude oil decalcifying agent. It has synergistic effect, stable performance, strong adsorption, high film forming strength, high film compactness and corrosion inhibition rate of over 90%, which can meet the anti-corrosion requirements of equipment and equipment. Moreover, the corrosion inhibitor is simple and easy to produce, and the energy consumption is small.
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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CA2822879A CA2822879C (en) | 2011-08-19 | 2012-04-27 | Mannich-base inhibitor for decalcification, preparation method and application thereof |
US13/990,389 US9399735B2 (en) | 2011-08-19 | 2012-04-27 | Mannich-base inhibitor for decalcification, preparation method and application thereof |
AP2013006943A AP3508A (en) | 2011-08-19 | 2012-04-27 | Mannich-base inhibitor for decalcification, preparation method and application thereof |
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CN201110240108.4 | 2011-08-19 | ||
CN201110240108.4A CN102953067B (zh) | 2011-08-19 | 2011-08-19 | 曼尼希碱脱钙缓蚀剂及其制备和应用 |
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PCT/CN2012/000566 WO2013026251A1 (zh) | 2011-08-19 | 2012-04-27 | 曼尼希碱脱钙缓蚀剂及其制备和应用 |
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US (1) | US9399735B2 (zh) |
CN (1) | CN102953067B (zh) |
AP (1) | AP3508A (zh) |
CA (1) | CA2822879C (zh) |
WO (1) | WO2013026251A1 (zh) |
Cited By (1)
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CN107201247A (zh) * | 2017-05-24 | 2017-09-26 | 广昌达新材料技术服务(深圳)股份有限公司 | 一种原油脱钙装置和脱钙方法 |
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CN104119850B (zh) * | 2013-04-24 | 2016-10-05 | 长江大学 | 一种用于盐水介质中的缓蚀剂及其制备方法 |
CN103865506B (zh) * | 2014-02-27 | 2017-01-11 | 山东泰和水处理科技股份有限公司 | 一种油气田高温酸化缓蚀剂及其制备方法 |
CN103881696B (zh) * | 2014-03-11 | 2016-09-14 | 山东聚鑫化工有限公司 | 高水溶性、耐高温曼尼希碱缓蚀剂中间体及制备方法 |
CN104497599B (zh) * | 2014-12-09 | 2017-05-17 | 中国石油大学(华东) | 一种微表处用沥青乳化剂及其制备方法 |
CN105885814A (zh) * | 2016-04-25 | 2016-08-24 | 中国石油集团渤海钻探工程有限公司 | 一种用于油气井酸化用缓蚀剂及其制备方法 |
CN106047326B (zh) * | 2016-06-03 | 2019-06-11 | 中国石油天然气股份有限公司 | 一种适用于高矿化度、高钡锶环境的co2驱缓蚀阻垢剂 |
CN108423843A (zh) * | 2018-02-06 | 2018-08-21 | 兰溪市哥特生物技术有限公司 | 一种低铬的水质缓蚀修复剂的制备方法 |
CN112877053B (zh) * | 2021-01-18 | 2023-02-07 | 西安石油大学 | 一种用于酸化压裂用中高温缓蚀剂及其制备方法 |
CN114806530B (zh) * | 2021-01-29 | 2023-05-26 | 中国石油天然气股份有限公司 | 一种高温酸化缓蚀剂及其制备方法和应用 |
CN113136198B (zh) * | 2021-04-07 | 2022-05-20 | 西安石油大油气科技有限公司 | 一种用于低渗透油田石油开采酸化用复合型缓冲剂 |
CN113106457A (zh) * | 2021-04-08 | 2021-07-13 | 四川瑞冬科技有限公司 | 一种缓蚀剂及其制备方法 |
CN115305160A (zh) * | 2022-09-01 | 2022-11-08 | 上海旭贵科技发展有限公司 | 一种溶出***清洗剂及其制备方法和应用 |
CN117512599B (zh) * | 2023-11-17 | 2024-04-12 | 武汉三友石化有限公司 | 一种耐温高缓蚀水溶性缓蚀剂的制备方法及其应用 |
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- 2012-04-27 AP AP2013006943A patent/AP3508A/xx active
- 2012-04-27 WO PCT/CN2012/000566 patent/WO2013026251A1/zh active Application Filing
- 2012-04-27 CA CA2822879A patent/CA2822879C/en active Active
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RU1550919C (ru) * | 1988-01-12 | 1992-10-15 | Предприятие П/Я А-1785 | Консервационный состав ВНИИНМ-ПАВ-31/87 |
CN1419573A (zh) * | 2000-03-24 | 2003-05-21 | 范蒂科公司 | 以烷基二亚丙基三胺为基础的曼尼希碱和其它化合物 |
CN101182296A (zh) * | 2007-12-14 | 2008-05-21 | 岳阳昌德化工实业有限公司 | 一种曼尼希碱及其制备方法和用途 |
CN102051622A (zh) * | 2010-12-28 | 2011-05-11 | 西安三环科技开发总公司 | 碳钢酸化缓蚀剂 |
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CN107201247A (zh) * | 2017-05-24 | 2017-09-26 | 广昌达新材料技术服务(深圳)股份有限公司 | 一种原油脱钙装置和脱钙方法 |
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CN102953067B (zh) | 2014-11-26 |
CN102953067A (zh) | 2013-03-06 |
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CA2822879C (en) | 2018-03-06 |
US20130256602A1 (en) | 2013-10-03 |
AP2013006943A0 (en) | 2013-06-30 |
US9399735B2 (en) | 2016-07-26 |
AP3508A (en) | 2016-01-04 |
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