EP0981572A1 - Polymerzusammensetzungen - Google Patents

Polymerzusammensetzungen

Info

Publication number
EP0981572A1
EP0981572A1 EP97924985A EP97924985A EP0981572A1 EP 0981572 A1 EP0981572 A1 EP 0981572A1 EP 97924985 A EP97924985 A EP 97924985A EP 97924985 A EP97924985 A EP 97924985A EP 0981572 A1 EP0981572 A1 EP 0981572A1
Authority
EP
European Patent Office
Prior art keywords
polymer
composition according
weight
surfactant
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97924985A
Other languages
English (en)
French (fr)
Inventor
Johannes Franciscus Hendrikus Braams
Marinus Johannes Reynhout
Bernardus Cornelis Maria In 't Veen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Infineum Holdings BV
Original Assignee
Infineum Holdings BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Infineum Holdings BV filed Critical Infineum Holdings BV
Publication of EP0981572A1 publication Critical patent/EP0981572A1/de
Withdrawn legal-status Critical Current

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    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C—CHEMISTRY; METALLURGY
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
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    • C10M145/40—Polysaccharides, e.g. cellulose
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    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • C10M157/00—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential
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    • C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/50—Aqueous dispersion, e.g. containing polymers with a glass transition temperature (Tg) above 20°C
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/12—Inorganic compounds
    • C10L1/1233—Inorganic compounds oxygen containing compounds, e.g. oxides, hydroxides, acids and salts thereof
    • C10L1/125—Inorganic compounds oxygen containing compounds, e.g. oxides, hydroxides, acids and salts thereof water
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    • 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
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
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    • C10L1/192—Macromolecular compounds
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    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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    • 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
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    • C10L1/234—Macromolecular compounds
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2362—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing nitrile groups
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    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/042—Sulfate esters
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • This invention relates to polymer compositions, their preparation and their use as pour-point depressants .
  • Crude oils may contain considerable amounts of wax. This wax gradually separates out as such materials are cooled, and at sufficiently low temperatures these materials may solidify completely. The lowest temperature observed during a standard laboratory test (ASTM D.97) at which the waxy material still flows is called the "pour-point" of the material.
  • Such polymers are typically polymers obtained by polymerisation of at least one olefinically unsaturated compound, which polymers contain aliphatic hydrocarbon side chains of at least 10 carbon atoms, e.g CIQ-30 aliphatic hydrocarbon side chains. Typically these polymers have molecular weights (M n ) in the range of 10,000 to 1,000,000. Examples of such polymers are described in
  • SHELLSWIM - 5X a 50%w solution of an alkyl acrylate polymer in xylene (having a pour point of 27°C)
  • SHELLSWIM - 11T a 50%w solution of an alkyl acrylate/vinyl pyridine copolymer in toluene (having a pour point of 18°C) .
  • a polymer composition comprising a dispersion of at least one polymer A obtained by polymerisation of at least one olefinically unsaturated compound, which polymer contains aliphatic hydrocarbon side chains of at least 10 carbon atoms, in a continuous aqueous phase comprising a surfactant and at least one polymer B which comprises a thixotropic hydrophilic polymer.
  • the polymer compositions according to the present invention advantageously display a low viscosity under transport conditions and a long term " storage stability.
  • Suitable polymers A are described in GB-A-1154966, GB-A-1161188, GB-A-1285087 , EP-A-0120512 , EP-A-0236844 and US-A-4547202. These polymers typically have molecular weights (M n ) in the range 10,000 to 1,000,000 and contain CIQ-30 aliphatic hydrocarbon side chains. Preferably polymer A has a molecular weight (M n ) in the range 20,000 to 250,000, more preferably 25,000 to 100,000, e.g. 30,000 to 80,000.
  • Polymer A is preferably a homo- or copolymer of one or more (C ⁇ g-30 n-alkyl) acrylates or methacrylates, e.g. 1-docosyl acrylate (C22) > 1-octadecyl acrylate (C_g) and 1-eicosyl acrylate (C20) •
  • Suitable copolymers are copolymers of one or more (C_g-30 n-alkyl) acrylates or methacrylates with a monoolefinically unsaturated compound having a nitrogen containing group, such as acrylonitrile, acrylamide, p-aminostyrene, N-vinylpyrrolidone or 4-vinylpyridine .
  • polymer A is a polymer of one or more (C ⁇ g_26 n-alkyl) acrylates or a copolymer of one or more (C_g-26 n-alkyl) acrylates and 4-vinyl- pyridine) .
  • non-ionic and ionic surfactants are suitable for incorporation in compositions according to the invention.
  • the surfactant is selected from alcohol ethoxy sulphate surfactants and lignosulphonate surfactants.
  • Such surfactants are typically alkali metal or ammonium salts.
  • Alcohol ethoxy sulphate surfactants typically have the formula
  • compositions according to the invention suitably contain 0.1 to 20, preferably 1 to 15, more preferably 1 to 10 parts by weight of surfactant per 100 parts by weight of polymer A.
  • Polymer B comprises a thixotropic hydrophilic polymer. Solutions of such polymers are known to have a high viscosity at a low shear rate and to have a low viscosity at a high shear rate. Suitable polymers B include for instance polysaccharides (e.g. Xanthan Gum) and partly hydrated polyacrylamides . These polymers typically have number average molecular weights (M n ) in the range 1 x 10 ⁇ to 1 x i F , preferably m the range 5 x 10 5 to 5 x 10 6 .
  • M n number average molecular weights
  • tnese polymers have a molecular weight distribution (M w /M n , whereby M w is defined as the weight average molecular weight) m the range 1 to 5, preferably 1 to 2, most preferably 1 to 1.5.
  • Polymer B is preferably a polysaccharide . Most preferably polymer B is Xanthan Gum.
  • compositions according to the invention suitably contain 0.01 to 20, preferably 0.1 to 10, more preferably 0.2 to 5, parts by weight of polymer B per 100 parts by weight of polymer A. These amounts include any minor amounts of solvents such as ethanol which may be present m the surfactant chosen for incorporation m the composition. Other additives may be incorporated m minor amounts m the compositions of the invention such as anti-oxidants, anti-corrosion agents or metal deactivators .
  • compositions according to the invention suitably contain more than 20, preferably more than 50, more preferably more than 80, parts by weight of water per 100 parts by weight of polymer A.
  • the continuous aqueous phase may comprise two or more different types of thixotropic hydrophilic polymers .
  • the invention further provides a process for the preparation of polymer compositions of the invention, which process comprises emulsifying a mixture of polymer A, the surfactant and polymer B at a temperature above the melting point of the polymer A, and cooling the resulting emulsion to a temperature below the melting temperature of polymer A.
  • the upper temperature limit for the process will be determined by the lowest decomposition temperature of the various components of the mixture. '.s.ing acrylate polymers as polymer A, alcohol ethoxy sulphate surfactants and/or lignosulphonate surfactants, and temperatures for emulsifying mixtures in the range 50°C to 100°C has been found to be very effective, temperatures in the range 60 to 100°C being preferred.
  • a composition of the invention in depressing the pour point of a crude mineral oil or a wax-containing fuel oil or diesel oil.
  • the polymer compositions of the invention have particularly useful application according to the invention in inhibition and/or reduction of wax deposition in crude oil pipelines.
  • the fact that the present aqueous compositions are fluid at lower temperatures than simple solutions of the relevant polymer at corresponding concentrations in solvents such as toluene or xylene confers significant improvements in handleability in lower temperature environments.
  • solvents such as toluene or xylene
  • the present aqueous formulations contain little or none of such solvents they constitute very attractive materials from the safety standpoint (flashpoint), when compared with conventional formulations.
  • Polymer I is an alkyl acrylate polymer, mp 51°C, of molecular weight (Mn) in the range 49,000 to 76,000 measured by gel permeation chromatography (GPC) (polyacrylate scale) prepared from a blend of linear alkyl acrylates comprising 1-docosyl acrylate, 1-octadecyl acrylate and 1-eicosyl acrylate.
  • GPC gel permeation chromatography
  • ethoxy sulphate is a 60%w solution in aqueous ethanol (2:1 w/w) of ammonium (C 2-15 alcohol) ethoxy sulphates containing 3 mol ethylene oxide/mol (density at 20°C 1.04 kg/1). Examples 1 to 6
  • Examples 2 to 6 were prepared in a similar manner to the above suspension, except that in Example 4 Xanthan gum was used instead of PHAM and that hexadecyltrimethylammonium bromide (HDTMAB) was used instead of ethoxysulphate; in comparative Example 5 glycerol was used instead of water and PHAM, the temperature of the thermostatic oil bath was 96°C and the mixture was emulsified for 2 minutes; and in comparative Example 6 glycerol was used instead of PHAM, the temperature of the thermostatic oil bath was 101°C and the mixture was gently emulsified for 1 minute, after which water was added. Details of all six suspensions and their preparation are given in Table 1.
  • suspensions were stable at ambient temperature (20°C) for at least one month.
  • the suspensions were all liquid at least down to 5°C .
  • the suspensions were tested by addition to a Far East crude oil and assessment of the pour point according to ASTM D.97.
  • the pour point of the undoped crude oil was 24°C, for examples 1-3, and 30°C for examples 4-6.
  • Viscosity was measured at 20 °C with a cone and plate system in a Carri-Med "CSL 500" Rheometer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP97924985A 1997-05-14 1997-05-14 Polymerzusammensetzungen Withdrawn EP0981572A1 (de)

Applications Claiming Priority (1)

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PCT/EP1997/002705 WO1998051731A1 (en) 1997-05-14 1997-05-14 Polymer compositions

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AU (1) AU3028997A (de)
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WO (1) WO1998051731A1 (de)

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AU2002360543A1 (en) 2001-12-11 2003-06-23 Southwest Research Institute Antitraction lubricious coating system
US7405184B2 (en) * 2001-12-11 2008-07-29 Southwest Research Institute Anti-traction, mobility denial methods and products
US7625848B2 (en) 2001-12-11 2009-12-01 Southwest Research Institute Anti-traction compositions
WO2006119296A1 (en) 2005-05-02 2006-11-09 Southwest Research Institute Methods for removing a dispersed lubricious coating from a substrate
CA2682144A1 (en) * 2007-04-13 2008-10-23 Basf Se Preparation and use of paraffin inhibitor formulations
GB0915683D0 (en) 2009-09-08 2009-10-07 Unilever Plc Branched high molecular weight addition polymers as viscosity reducers
EP3426702B1 (de) * 2016-03-10 2019-10-30 Basf Se Wässrige polymerdispersionen, verfahren zu deren herstellung und verwendung davon als giesspunktunterdrücker für rohöl, erdöl und erdölprodukte
EP3551718B1 (de) 2016-12-07 2021-10-13 Basf Se Wässrige zusammensetzungen von paraffininhibitoren
EP3412691A1 (de) 2017-06-07 2018-12-12 Rhodia Operations Polymerdispersionen zur wachshemmung
MX2020002740A (es) * 2017-09-11 2020-07-21 Basf Corp Dispersiones polimericas acuosas, un metodo para su preparacion y uso como depresores del punto de vertido para petroleo crudo, petroleo y productos de petroleo.
AU2019372111A1 (en) 2018-11-02 2021-06-03 Energy Solutions (US) LLC Polymer dispersions for wax inhibition during stimulation treatment
WO2023025636A1 (en) 2021-08-27 2023-03-02 Basf Se Aqueous dispersions of paraffin inhibitors

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AU3028997A (en) 1998-12-08

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