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WO2005073277A1 - Polyamines de polyethylene substituees, procede pour les preparer et utilisation de celles-ci - Google Patents

Polyamines de polyethylene substituees, procede pour les preparer et utilisation de celles-ci Download PDF

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Publication number
WO2005073277A1
WO2005073277A1 PCT/SK2005/000002 SK2005000002W WO2005073277A1 WO 2005073277 A1 WO2005073277 A1 WO 2005073277A1 SK 2005000002 W SK2005000002 W SK 2005000002W WO 2005073277 A1 WO2005073277 A1 WO 2005073277A1
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moles
general formula
reaction
brought
polyethylene polyamines
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Ceased
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PCT/SK2005/000002
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English (en)
Inventor
Milan Kucera
Magdalena Harustakova
Frantisek Masarovic
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SLOVNAFT VURUP AS
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SLOVNAFT VURUP AS
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0206—Polyalkylene(poly)amines
    • C08G73/0213—Preparatory process
    • 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
    • C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G9/14—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils in pipes or coils with or without auxiliary means, e.g. digesters, soaking drums, expansion means
    • C10G9/16—Preventing or removing incrustation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/16—Reaction products obtained by Mannich reactions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1826—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms poly-hydroxy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/20—Organic compounds containing halogen
    • C10L1/201—Organic compounds containing halogen aliphatic bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/043—Mannich bases

Definitions

  • the invention relates to substituted polyethylene polyamines, method of their preparation and their use as inhibitors of formation of resins and coke in pyrolysis processes, where they form undesired deposits in piping of pyrolysis furnaces during thermal cracking of hydrocarbon residues, such as primary vacuum residues, vacuum residues from hydrogenation cracking, non-converted oils from the process of hydrogenation cracking, and also various distillation layers of primary vacuum distillates and distillates from the process of hydrogenation cracking and non-converted fractions from the process of fluid catalytic cracking in processing of petroleum.
  • hydrocarbon residues such as primary vacuum residues, vacuum residues from hydrogenation cracking, non-converted oils from the process of hydrogenation cracking, and also various distillation layers of primary vacuum distillates and distillates from the process of hydrogenation cracking and non-converted fractions from the process of fluid catalytic cracking in processing of petroleum.
  • the external shell of a micelle consists of hydrocarbon molecules. If the concentration of resins is sufficient, asphaltenes are peptized and they do not come out from the system. If the concentration of resins on the surface of micelles is low, they mutually interact and they form a network, gel-like structure. With further increase of concentration of asphaltenes, or after addition of a hydrocarbon, asphaltenes coagulate and precipitate.
  • Additives for the mentioned use are required to have detergent and stabilizing influence on the colloid system of micelles with asphaltenic cores, and if possible, simultaneously also the ability to block the transfer of carbenium ions.
  • Highly effective additives posses both properties at once.
  • Effective compounds are for example compounds of alkylsulfonic acids type, some aminophenols and N-alkylamine compounds, which has primarily detergent effect, or some naphthene acids and their salts, especially molybdenum and cobalt salts, which block the transfer of carbenium cation.
  • Subject of the present invention are substituted polyethylene polyamines, method of their preparation and their use as additives inhibiting or limiting the formation of deposits in the process of hydrocarbon residues cracking, which simultaneously prevent creation of coke precursors, being especially asphaltenes, and which absorb free radicals affecting mainly stability of products in during their separation and storage.
  • Compounds, which are subject of this invention due to their ability to inhibit transfer of carbenium ion, affect also cracking of the hydrocarbon residues in the reaction section. They do not influence the activity of catalysts used in the cracking process and thus they do not affect yield of the process.
  • the additives are soluble in aromatic solvents as for example xylene, toluene, benzene, and in strong polar organic solvents as methanol, ethanol, butanol, cyclohexanol, in polyvalent alcohols as for example glycol, propylene glycol and other polyvalent alcohols, further in chlorohydrocarbons as for example chlorofom, tetrachlormethane, trichlorethylene etc.
  • aromatic solvents as for example xylene, toluene, benzene, and in strong polar organic solvents as methanol, ethanol, butanol, cyclohexanol
  • polyvalent alcohols as for example glycol, propylene glycol and other polyvalent alcohols
  • chlorohydrocarbons as for example chlorofom, tetrachlormethane, trichlorethylene etc.
  • Optimal effective concentration ranges from 10 to 1500 ppm. It is desired the additive concentrations to be as low as possible
  • Effectiveness of the additives can be tested using the following methods: 1. Test with membrane filter - medium distillate with the additive under thermal stress is compared with a sample of medium distillate without the additive. After the test, samples are filtered through membrane filter and a color change of the filtrate and the amount of sediments on the filter compared. 2. Sedimentation test (accelerated) - a sample of medium distillate with the additive and without the additive are thermally stressed in given time interval, and simultaneously oxidized by air stream. At the end of the time interval samples are filtered and a color change of the filtrate and the amount of sediments on the filter compared. 3. Hot test (thermal test) - samples of medium distillate with the additive and without the additive are thermally stressed in given time interval.
  • compounds effective as antifouling additives are in general linear alkyl- or aryl- substituted polyethylene polyamines having general formula (I):
  • Compounds of this type with identified inhibiting or restricting influence on coke formation in pyrolysis furnaces for cracking of hydrocarbon residues are prepared by poly-condensation of linear polyethylene polyamines with formaldehyde or by multistage reaction of linear polyethylene polyamines with properly selected number of ethylenamine - mers -(CH2-CH2-NH)- with formaldehyde and phenol, which can be further substituted on benzene core by reaction with formaldehyde and alkylamines having suitable length of ending alkylsubstitutes R ⁇ , R2, R3, R4.
  • phenols which are substituted in meta or para position, so that the orto position on the benzene core is not deactivated.
  • suitable substituents are alkyl-, aryl-, aminoaryl, nitro-group, heterocyclic compound or amide.
  • phenol 1-naphtol and its similar arylalcohols can be used.
  • Structure of the additives according to present invention is mainly defined by: 1. the type of used polyethylene polyamine i.e. the number of -mers - (CH2-CH2-NH)-, by the type of substitution of end groups of polyethylene polyamine, and by the number of carbons in alkylsubstituent, 2. the molar ratio of polyethylene polyamine to formaldehyde used in the reaction, 3. the number of stages of the poly-condensation reaction of polyethylene polyamines with formaldehyde, 4. the number of subsequent stages of the poly-condensation reactions of the product of polycondensation of polyethylene polyamine, in the first, respectively in the second stage of reaction with phenol and formaldehyde.
  • the most suitable solvent for synthesis and application of the additives is xylene.
  • xylene another aromatic solvents can also be used, e.g. benzene, tholuene, mezitylene, and the medium distillates e.g. kerosene or gas oil, heavy gasoline or pyrolysis gasoline.
  • Compounds having general structural formula (I), of which some typical compounds are presented in the examples 1 to 5 of modes for carrying out the invention, can be used according to present invention as additives individually, or as mixtures of selected compounds, for the process of cracking of residues, in such an amount, that the sum of concentrations of the additives in the raw mixture for cracking of hydrocarbon residues from oil processing is in the range from 10 to 1000 ppm.
  • Individual additives or their mixtures in mentioned solvents are continuously added to streams of raw materials, streams of intermediate products, and products from hydrogenation cracking of residues.
  • the sum of concentrations of active compounds in the concentrates of additives can vary from 1 to 95 % by weight.
  • compounds having general structural formula (I) can be used as additives to raw materials, and product streams of the operated technological devices as well as to stored products and intermediate products.
  • Mode(s) for carrying out the invention [0022] Following modes for carrying out the invention present methods of preparation of the exemplary types of compounds having general structural formula (I), usable as additives inhibiting or limiting formation of resins and coke in the equipment for thermal cracking of hydrocarbon residues, such as primary vacuum residues, vacuum residues from hydrogenation cracking, non-converted oil from hydrogenation cracking, as well various distillation layers of primary vacuum distillates and distillates from hydrogenation cracking, and non-converted fractions from the fluid catalytic cracking during processing of petroleum, and method of their use.
  • hydrocarbon residues such as primary vacuum residues, vacuum residues from hydrogenation cracking, non-converted oil from hydrogenation cracking, as well various distillation layers of primary vacuum distillates and distillates from hydrogenation cracking, and non-converted fractions from the fluid catalytic cracking during processing of petroleum, and method
  • Amounts of 250g of xylene, 25.8g of diethylene triamine and 134g of octadecylamine are charged to 5-liter reactor with stirrer, reverse cooler and temperature regulation.
  • 40 g of 37% water solution of formaldehyde is gradually added at such a rate that the mixture temperature does not exceed 30°C.
  • reaction mixture, continuously stirred is retained at the temperature within 30 to 35°C for 2 hours.
  • reaction water is removed by azeotropic distillation. Distillation is finished when pure xylene without water starts to distill. The product is suitable for use as inhibiting additive.
  • Example 2 [0025] Amounts of 250g of xylene, 94g of phenol and 52g of diethylene triamine are charged to 5-liter reactor with stirrer, reverse cooler and temperature regulation. To the mixture, 83 g of 37% water solution of formaldehyde is gradually added at such a rate that the mixture temperature does not exceed 35°C. After adding the formaldehyde, reaction mixture, continuously stirred, is retained at the above temperature for 2 hours. + H ⁇ 2 . — CH j — CH 2 — H— CH2- CH2 ⁇ NH 2 + 2 HCHO
  • reaction water is removed by azeotropic distillation. Distillation is finished when pure xylene without water starts to distill. The product is suitable for use as inhibiting additive.
  • Amounts of 600g of xylene, 94g of phenol and 111 g of diethylene triamine are charged to 5-liter reactor with stirrer, reverse cooler and temperature regulation. Mixture is heated to 35°C and 80g of 37% water solution of formaldehyde is gradually added at such a rate that the mixture temperature does not exceed 40"C. After adding the formaldehyde, reaction mixture, continuously stirred, is retained at the temperature within 35 to 40°C for 2 hours.
  • reaction water is removed by azeotropic distillation. Distillation is finished when pure xylene without water starts to distill. The product is used as input for the second stage of the reaction.
  • Amounts of 600g of xylene, 94g of phenol and 51 g of diethylene triamine are charged to 5-liter reactor with stirrer, reverse cooler and temperature regulation.
  • 162g of 37% water solution of formaldehyde is dosed at such a rate that the mixture temperature does not exceed 38°C.
  • reaction mixture continuously stirred, is retained at the temperature within 35 to 40°C for 2 hours.
  • Reaction water is removed by azeotropic distillation. Distillation is finished when pure xylene without water starts to distill. The product is used as input for the second stage of the reaction.
  • Amounts of 600g of xylene, 94g of phenol and 51 g of diethylene triamine are charged to 5-liter reactor with stirrer, reverse cooler and temperature regulation.
  • 162g of 37 % water solution of formaldehyde is gradually added at such a rate that the mixture temperature does not exceed 38°C.
  • reaction mixture continuously stirred, is retained at the temperature within 35 to 40°C for 2 hours.
  • Reaction water is removed by azeotropic distillation. Distillation is finished when pure xylene without water starts to distill. The product is used as input for the second stage of the reaction.
  • reaction mixture 162g of 37% water solution of formaldehyde is gradually added in such a rate that the mixture temperature does not exceed 50°C.
  • reaction mixture continuously stirred, is retained at the temperature 50°C for 2 hours.
  • Reaction water is removed by azeotropic distillation. Distillation is finished when pure xylene without water starts to distill.
  • the product is suitable for use as inhibiting additive.
  • Present invention is industrially applicable in synthesis and use of compounds effective as additives inhibiting, or limiting the formation of coke, or resins in equipment for thermal cracking of hydrocarbon residues, such as vacuum residues, vacuum residues from the processes of hydrogenation cracking, non-converted oils from the process of hydrogenation cracking, and various distillation layers of primary vacuum distillates and distillates from the process of hydrogenation cracking and non-converted fractions from the process of fluid catalytic cracking from processing of petroleum.
  • hydrocarbon residues such as vacuum residues, vacuum residues from the processes of hydrogenation cracking, non-converted oils from the process of hydrogenation cracking, and various distillation layers of primary vacuum distillates and distillates from the process of hydrogenation cracking and non-converted fractions from the process of fluid catalytic cracking from processing of petroleum.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

La présente invention concerne des polyamines de polyéthylène substituées qui présentent la formule générale (I), un procédé pour les préparer, ainsi que leur utilisation en tant qu'additifs inhibant ou limitant la formation de dépôts lors du processus de craquage de résidus d'hydrocarbure, qui empêchent simultanément la formation de précurseurs de coke, notamment des asphaltènes, et se lient à des radicaux libres qui modifient de manière importante la stabilité des produits lors de leur séparation et de leur stockage.
PCT/SK2005/000002 2004-01-30 2005-01-31 Polyamines de polyethylene substituees, procede pour les preparer et utilisation de celles-ci Ceased WO2005073277A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SK75-2004A SK286537B6 (sk) 2004-01-30 2004-01-30 Substituované polyetylénpolyaminy, spôsob ich prípravy a použitia
SKPP75-2004 2004-01-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8876921B2 (en) 2007-07-20 2014-11-04 Innospec Limited Hydrocarbon compositions
JP2021004270A (ja) * 2019-06-25 2021-01-14 住友ベークライト株式会社 フェノール樹脂

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3316177A (en) * 1964-12-07 1967-04-25 Lubrizol Corp Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene
US4025316A (en) * 1974-11-06 1977-05-24 Exxon Research And Engineering Company Mannich base reaction products useful as liquid hydrocarbon additives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3316177A (en) * 1964-12-07 1967-04-25 Lubrizol Corp Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene
US4025316A (en) * 1974-11-06 1977-05-24 Exxon Research And Engineering Company Mannich base reaction products useful as liquid hydrocarbon additives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WANG, PINGSHAN; XIE, YONGSHU; KOU, FUPING; LIN, RUISEN; ZONG, HANXING: "Synthesis of polyaminodiphenol ligands and study on their complexes with Zn(II)", HUAXUE YANJIU YU YINGYONG, vol. 10, no. 5, 1998, pages 534 - 538, XP009047002 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8876921B2 (en) 2007-07-20 2014-11-04 Innospec Limited Hydrocarbon compositions
JP2021004270A (ja) * 2019-06-25 2021-01-14 住友ベークライト株式会社 フェノール樹脂

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SK286537B6 (sk) 2008-12-05

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