US20050085588A1 - Acrylic polymer latex dispersions as additives for inhibiting paraffin deposits in crude oils and compositions containing same - Google Patents

Acrylic polymer latex dispersions as additives for inhibiting paraffin deposits in crude oils and compositions containing same Download PDF

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Publication number
US20050085588A1
US20050085588A1 US10/486,655 US48665504A US2005085588A1 US 20050085588 A1 US20050085588 A1 US 20050085588A1 US 48665504 A US48665504 A US 48665504A US 2005085588 A1 US2005085588 A1 US 2005085588A1
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Prior art keywords
weight
monomers
meth
vinyl
parts
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US10/486,655
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Inventor
Alain Baloche
Didier Juhue
Philippe Picard
Tong Pou
Caroline Truszkowski
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Arkema France SA
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Atofina SA
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Assigned to ATOFINA reassignment ATOFINA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TRUSZKOWSKI, CAROLINE, POU, TONG EAK, BALOCHE, ALAIN, PICARD, PHILIPPE, JUHUE, DIDIER
Publication of US20050085588A1 publication Critical patent/US20050085588A1/en
Priority to US11/334,350 priority Critical patent/US20060183843A1/en
Priority to US11/802,716 priority patent/US7790821B2/en
Abandoned legal-status Critical Current

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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
    • C10L1/2468—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained by reactions involving only carbon to carbon unsaturated bonds; derivatives thereof
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2666—Organic compounds containing phosphorus macromolecular compounds
    • C10L1/2675—Organic compounds containing phosphorus macromolecular compounds obtained by reactions involving only carbon to carbon unsaturated bonds; derivatives thereof

Definitions

  • the technical field of this invention is that of crude petroleum hydrocarbons and additives that are intended to improve their conditions of use.
  • the crude petroleum hydrocarbons can contain significant paraffin fractions, of which the amount and the exact nature are variable according to the extraction fields.
  • the paraffins are liquid and dissolved in the crude oil.
  • the paraffins by crystallizing, form a three-dimensional grid of needles and flakes. This results in a loss of fluidity that makes the production, the transport, the storage and even the treatment of these oils very difficult.
  • the clogging in the pipelines and treatment equipment is frequent.
  • U.S. Pat. No. 5,418,278 or EP 359,061 of HENKEL proposes resolving a portion of these drawbacks by emulsions that can reach 30 to 50% of dry extract that contains n-alkyl acrylate copolymers and unsaturated ethylene derivatives of carboxylic acid or anhydride in the presence of a surfactant.
  • This invention proposes dispersions of acrylic copolymer latex with a variable composition that are particularly suited for the reduction of the pour point of the crude petroleum hydrocarbons.
  • the latex dispersions of this invention comprise at least 100 parts by weight of components (1) to (4) below:
  • a co-solvent or a mixture of co-solvents preferably 5 to 25, and advantageously 5 to 20, parts by weight, selected from among the ketones such as methylethylketone or methylisobutylketone, the aromatic solvents such as toluene, xylene and the mixtures of aromatic hydrocarbons, the alcohols such as butanol or isopropanol, the glycols and polyglycol ethers such as ethylene or propylene glycol, diethylene glycol or dipropylene glycol.
  • a co-solvent or a mixture of co-solvents preferably 5 to 25, and advantageously 5 to 20, parts by weight, selected from among the ketones such as methylethylketone or methylisobutylketone, the aromatic solvents such as toluene, xylene and the mixtures of aromatic hydrocarbons, the alcohols such as butanol or isopropanol, the glycols and polyglycol ethers such as
  • surfactants ionic surfactants and/or nonionic surfactants and/or protective colloids such as polyvinyl alcohols and/or amphiphilic polymers that are selected from among the sulfates or sulfonates of fatty alcohols or alkylphenol, but also the alkylbenzene sulfonates and sulfosuccinates, the quaternary ammonium salts such as dimethyldialkylammonium chlorides and ethoxylated fatty alcohols).
  • surfactants ionic surfactants and/or nonionic surfactants and/or protective colloids
  • polyvinyl alcohols and/or amphiphilic polymers that are selected from among the sulfates or sulfonates of fatty alcohols or alkylphenol, but also the alkylbenzene sulfonates and sulfosuccinates, the quaternary ammonium salts such as dimethyldialkylammonium chlorides and eth
  • dispersions that comprise as co-solvent(s) at least one or more liquid polyols, those whose amount of water represents more than 40 and advantageously more than 50% by weight of solid polyol(s) are preferred.
  • the latex dispersions according to the invention are obtained by a process for emulsion polymerization in water in the presence of surfactant(s) and optionally in the presence of co-solvent(s).
  • the radical-type polymerization in emulsion is conducted in a standard manner in a device that is known for polymerizations in emulsion according to a batch process, semi-batch process or continuous process.
  • the scope of the invention would not be exceeded by using a Manton-Gaulin-type high-pressure emulsifier or by using an ultrasound technique to emulsify the mixture before polymerization and to adopt a so-called mini-emulsion or mini-dispersion process so as to reduce the amounts of organic co-solvents and surfactants.
  • Initiating agents are used that produce free radicals that are selected from among the usual peroxides, such as the persulfates, for example potassium or ammonium persulfate, the organic hydroperoxides and peroxides, hydrogen peroxide, peracids, the diazo compounds, for example 4,4′ azobis(4-cyanopentanoic) acid or 2,2′ azobis (2-amidinopropane) hydrochloride.
  • peroxides such as the persulfates, for example potassium or ammonium persulfate
  • the organic hydroperoxides and peroxides hydrogen peroxide, peracids
  • the diazo compounds for example 4,4′ azobis(4-cyanopentanoic) acid or 2,2′ azobis (2-amidinopropane) hydrochloride.
  • a redox system for example ammonium persulfate that is combined with sodium metabisulfite to work at a lower temperature.
  • the polymerization reaction can be conducted over a temperature range of 20 to 90° C. for 0.5 to 4 hours according to the initiating conditions selected.
  • Buffering agents such as, for example, sodium tetraborate
  • transfer agents such as, for example, alkyl mercaptans
  • the performance level of the products of the invention can also be improved in particular by the post-addition of the organic solvents cited above, but also surfactants that are also cited with, in addition, those of low HLB (used to ensure hydrophilic-lipophilic balance), preferably less than or equal to 5, such as the fatty sorbitan esters.
  • the performance levels of the products according to the invention have been assessed thanks to the measurement of the pour point according to the ASTM D97 standard that consists in adding the crude oil that is brought to a temperature that is higher than its pour point, with a defined amount of additive for the inhibition of the deposition of paraffin, then in cooling the crude in stages of 3° C., whereby the pour point represents the temperature starting from which the crude oil no longer flows.
  • a HERZOG MP852 device was used, whose detection of the flow is ensured by an LCD camera.
  • reaction After the exothermy peak, the reaction is allowed to take place for 2 hours, then it is cooled to ambient temperature.
  • the latex dispersion that is thus obtained and that is named S1 is used as is.
  • the medium is brought to 105° C., and within one hour, 3.8 g of t-butyl perbenzoate that is marketed by Atofina under the name Trigonox C in solution in 12 g of a fraction of aromatic hydrocarbons with a boiling point of 180-200° C. (Solvesso 150) is added.
  • the medium is then kept for 2 hours at 105° C. to ensure the complete conversion of the acrylic monomer.
  • Solutions S1 and S2 are respectively added to the Itteville crude at variable concentrations, and pour points (PE) of the crude oils that are thus added are measured according to the method that is described above.
  • the table below lists the values of the pour point that are expressed in ° C.
  • Concentration* (ppm) 0 100 200 500 PE(S1) 12 ⁇ 12 ⁇ 18 ⁇ 27 PE(S2) 12 ⁇ 9 ⁇ 9 ⁇ 15 *The concentration is expressed in equivalent terms of the product of Comparison Example 1 with 55% dry extract.
  • dispersion S1 is a very effective additive for lowering the pour point of the Itteville crude oil without requiring any dilution for its use.
  • the procedure is performed according to the operating mode that is described in Example 1, but by eliminating the monomethyl ether dipropylene glycol and by replacing a portion of the 169 g of behenyl acrylate by 25 g of N-vinyl pyrrolidone.
  • the latex dispersion that is thus obtained as is, named S3, is used to add the Itteville crude.
  • the table below lists the values of the pour point expressed in ° C. Concentration* (ppm) 0 500 PE(S3) 12 ⁇ 18 *The concentration is expressed in equivalent terms of the production of Comparison Example 1 with 55% dry extract.
  • solution S3 according to the invention added to the Itteville crude, lowers in particular the pour point as the table above shows.
  • reaction After the exothermy peak, the reaction is allowed to take place for 2 hours, then it is cooled to ambient temperature.
  • solution S4 added to the Itteville crude, reduces in particular the pour point.
  • Example 1 The synthesis that is described in Example 1 is resumed, but during the cooling, 1.7 and 3.4 g respectively of a non-ionic surfactant of ethoxylated fatty alcohol-type (marketed by the CECA Company under the name Remcopal 10) are post-added to obtain solutions S5 and S6 respectively.
  • the solidification points (PF) of these solutions have been measured in the same way as the pour points of the crude oils.
  • the table below combines the values of the solidification points of S5 and S6 as well as that of solution S1:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US10/486,655 2001-08-08 2002-08-02 Acrylic polymer latex dispersions as additives for inhibiting paraffin deposits in crude oils and compositions containing same Abandoned US20050085588A1 (en)

Priority Applications (2)

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US11/334,350 US20060183843A1 (en) 2001-08-08 2006-01-19 Dispersions of acrylic polymer latex as additives for the inhibition of the deposition of paraffins in crude oils and compositions that contain them
US11/802,716 US7790821B2 (en) 2001-08-08 2007-05-24 Dispersions of acrylic polymer latex as additives for the inhibition of the deposition of paraffins in crude oils and compositions that contain them

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0110591A FR2828494B1 (fr) 2001-08-08 2001-08-08 Dispersions de latex de polymeres acryliques comme additifs pour l'inhibition du depot de paraffines dans les huiles brutes et compositions les contenant
FR0110591 2001-08-08
PCT/FR2002/002786 WO2003014170A1 (fr) 2001-08-08 2002-08-02 Dispersions de latex de polymeres acryliques comme additifs pour l'inhibition du depot de paraffines dans les huiles brutes et compositions les contenant

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US11/334,350 Abandoned US20060183843A1 (en) 2001-08-08 2006-01-19 Dispersions of acrylic polymer latex as additives for the inhibition of the deposition of paraffins in crude oils and compositions that contain them
US11/802,716 Expired - Fee Related US7790821B2 (en) 2001-08-08 2007-05-24 Dispersions of acrylic polymer latex as additives for the inhibition of the deposition of paraffins in crude oils and compositions that contain them

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US11/802,716 Expired - Fee Related US7790821B2 (en) 2001-08-08 2007-05-24 Dispersions of acrylic polymer latex as additives for the inhibition of the deposition of paraffins in crude oils and compositions that contain them

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US (3) US20050085588A1 (de)
EP (1) EP1421123B1 (de)
CN (2) CN1564831A (de)
CA (1) CA2457768A1 (de)
EA (1) EA020725B1 (de)
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FR (1) FR2828494B1 (de)
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US20050215437A1 (en) * 2004-03-26 2005-09-29 Shmakova-Lindeman Olga E Paraffin inhibitors
US20080097016A1 (en) * 2004-09-27 2008-04-24 Tadych John E Differential Adhesion Masking Composition
US20080249207A1 (en) * 2006-05-02 2008-10-09 Whiteley Corporation Pty Ltd Safety Coatings
US20090264585A1 (en) * 2004-10-15 2009-10-22 Avramidis Kostas S Emulsion polymerization of hydrophobic monomers
US20100025290A1 (en) * 2006-12-22 2010-02-04 Clariant Finance (Bvi) Limited Dispersions Of Polymer Oil Additives
US20220041917A1 (en) * 2018-11-02 2022-02-10 Rhodia Operations Polymer dispersions for wax inhibition during stimulation treatment

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FR2859211B1 (fr) * 2003-08-28 2006-01-21 Ceca Sa Compositions sous forme d'emulsions stables, leurs preparations et leurs utilisation pour l'abaissement du point d'ecoulement des huiles brutes et l'inhibition du depot de paraffines
CN100386350C (zh) * 2005-08-25 2008-05-07 颜奇旭 反光膜用丙烯酸树脂乳液及其制备方法
CN100391990C (zh) * 2005-12-08 2008-06-04 西南石油学院 一种水溶性分子间缔合型三元疏水缔合聚合物及其合成方法
CN101311242B (zh) * 2007-05-24 2012-02-15 西部钻探克拉玛依钻井工艺研究院 一种羟基酸盐钻井液
CN101353569B (zh) * 2008-09-17 2011-06-29 西南石油大学 一种油田用可控制交联凝胶堵水堵漏材料
CN101602941B (zh) * 2009-07-14 2012-02-01 辽宁瑞达石油技术有限公司 一种广谱原油防蜡降凝剂
WO2013170411A1 (en) * 2012-05-14 2013-11-21 Celanese International Corporation Vinyl acetate-ethylene copolymer emulsion and paper coating composition based on the same
US20130340325A1 (en) 2012-06-22 2013-12-26 Baker Hughes Incorporated Charged Block Co-polymers as Pour Point Depressants
CN103614128A (zh) * 2013-11-11 2014-03-05 中国石油天然气集团公司 一种应用于三次采油油井的微乳液重质蜡晶乳化分散剂
CN103897083A (zh) * 2014-03-04 2014-07-02 哈尔滨绿科科技有限公司 一种多领域用高性能环保乳胶及其制备方法和应用
CN103897680B (zh) * 2014-04-14 2017-04-05 中国石油大学(北京) 一种油溶性沥青质分散解堵剂
WO2017182574A1 (de) 2016-04-21 2017-10-26 Universität Hamburg Rohölzusammensetzung, umfassend ein additiv zur verbesserung der fliesseigenschaften von paraffinhaltigem rohöl
CA3048363A1 (en) 2017-03-30 2018-10-04 Clariant International Ltd Fluids for fracking of paraffinic oil bearing formations
EP3412691A1 (de) 2017-06-07 2018-12-12 Rhodia Operations Polymerdispersionen zur wachshemmung
CN111344313A (zh) 2017-09-11 2020-06-26 巴斯夫公司 水性聚合物分散体、其制备方法及其作为原油、石油和石油产品的倾点下降剂的用途
EA039742B1 (ru) 2017-09-20 2022-03-05 Клариант Интернэшнл Лтд Дисперсии полимерных присадок к нефти
CN110283580B (zh) * 2019-06-28 2021-04-20 中国石油大学(华东) 降凝防蜡剂及其制备方法
CN110437371A (zh) * 2019-08-28 2019-11-12 西南石油大学 一种四元聚合物油溶性原油降凝剂及制备方法
BR112022018743A2 (pt) 2020-03-26 2022-11-01 Evonik Operations Gmbh Dispersão de polímero, seu processo de preparação e uso
US20230103215A1 (en) 2020-03-26 2023-03-30 Evonik Operations Gmbh Polymer dispersion made from (meth)acrylates having long side chains
CN113999663A (zh) * 2021-10-11 2022-02-01 天津大港油田滨港集团博弘石油化工有限公司 一种稠油降粘剂及其制备方法
WO2023200839A1 (en) * 2022-04-12 2023-10-19 Championx Usa Inc. Solid paraffin inhibitor and corrosion inhibitor compositions

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US5418278A (en) * 1988-09-10 1995-05-23 Henkel Kommanditgesellschaft Auf Aktien Aqueous emulsion copolymers, more especially in water-and oil-dilutable form, for improving the flow properties and pour point depression of crude oils and petroleum fractions and their use

Cited By (12)

* Cited by examiner, † Cited by third party
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US20050215437A1 (en) * 2004-03-26 2005-09-29 Shmakova-Lindeman Olga E Paraffin inhibitors
US7417009B2 (en) * 2004-03-26 2008-08-26 Nalco Company Paraffin inhibitors
US20080097016A1 (en) * 2004-09-27 2008-04-24 Tadych John E Differential Adhesion Masking Composition
US20090264585A1 (en) * 2004-10-15 2009-10-22 Avramidis Kostas S Emulsion polymerization of hydrophobic monomers
US20080249207A1 (en) * 2006-05-02 2008-10-09 Whiteley Corporation Pty Ltd Safety Coatings
EP2029680A1 (de) * 2006-05-02 2009-03-04 Whiteley Corporation Pty Ltd Sicherheitsbeschichtungen
EP2029680A4 (de) * 2006-05-02 2010-10-20 Whiteley Corp Pty Ltd Sicherheitsbeschichtungen
US20100025290A1 (en) * 2006-12-22 2010-02-04 Clariant Finance (Bvi) Limited Dispersions Of Polymer Oil Additives
US8293690B2 (en) 2006-12-22 2012-10-23 Clariant Finance (Bvi) Limited Dispersions of polymer oil additives
US8598101B2 (en) 2006-12-22 2013-12-03 Clariant Finance (Bvi) Limited Dispersions of polymer oil additives
US20220041917A1 (en) * 2018-11-02 2022-02-10 Rhodia Operations Polymer dispersions for wax inhibition during stimulation treatment
US11618845B2 (en) * 2018-11-02 2023-04-04 Rhodia Operations Polymer dispersions for wax inhibition during stimulation treatment

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US20060183843A1 (en) 2006-08-17
CN1564831A (zh) 2005-01-12
CA2457768A1 (fr) 2003-02-20
EP1421123A1 (de) 2004-05-26
FR2828494A1 (fr) 2003-02-14
NO20040972L (no) 2004-03-05
EA200400190A1 (ru) 2004-06-24
WO2003014170A1 (fr) 2003-02-20
EA020725B1 (ru) 2015-01-30
ES2394416T3 (es) 2013-01-31
EP1421123B1 (de) 2012-09-19
US7790821B2 (en) 2010-09-07
FR2828494B1 (fr) 2005-06-03

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