US3904385A - Polyacrylates and waxy residual fuel compositions thereof - Google Patents

Polyacrylates and waxy residual fuel compositions thereof Download PDF

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Publication number
US3904385A
US3904385A US250900A US25090072A US3904385A US 3904385 A US3904385 A US 3904385A US 250900 A US250900 A US 250900A US 25090072 A US25090072 A US 25090072A US 3904385 A US3904385 A US 3904385A
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United States
Prior art keywords
alkyl
poly
wax
pour
residual
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Expired - Lifetime
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US250900A
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English (en)
Inventor
William M Sweeney
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Texaco Inc
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Texaco Inc
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Filing date
Publication date
Application filed by Texaco Inc filed Critical Texaco Inc
Priority to US250900A priority Critical patent/US3904385A/en
Priority to DE2264328A priority patent/DE2264328A1/de
Priority to AR247454A priority patent/AR208270A1/es
Priority to ZA731515A priority patent/ZA731515B/xx
Priority to GB1126873A priority patent/GB1368729A/en
Priority to AU53306/73A priority patent/AU466151B2/en
Priority to CA166,622A priority patent/CA987492A/en
Priority to CA166,621A priority patent/CA1020533A/en
Priority to CA166,624A priority patent/CA1020534A/en
Priority to NL7303927A priority patent/NL7303927A/xx
Priority to CA166,623A priority patent/CA992697A/en
Priority to AT254673A priority patent/AT329170B/de
Priority to CH438973A priority patent/CH582232A5/xx
Priority to SE7304294A priority patent/SE396403B/xx
Priority to NO1282/73A priority patent/NO137864C/no
Priority to FR7314133A priority patent/FR2190850B1/fr
Priority to BE130233A priority patent/BE798484A/xx
Priority to JP48045230A priority patent/JPS4926303A/ja
Priority to BR324573A priority patent/BR7303245D0/pt
Priority to IT23828/73A priority patent/IT987198B/it
Priority to ES414436A priority patent/ES414436A1/es
Priority to US05/553,182 priority patent/US3951929A/en
Application granted granted Critical
Publication of US3904385A publication Critical patent/US3904385A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • C10L1/18—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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—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 type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • ABSTRACT An interpolymeric poly(n-alkylacrylate) of a molecular weight between about 3000 and 100,000 wherein said alkyl is of at least 18 carbons and at least 70 wt. of said alkyl is of between 20 and 24 carbons inclusively, the C to C alkyl group consisting of between about 2 and 65 wt. of C alkyl, between about 18 and 65 wt. C alkyl, and between about 8 and 35 wt. C alkyl; and a residual petroleum fuel containing between 4 and 15 wt. macrocrystalline paraffin wax having incorporated therein a pour depressing amount of said poly (n-alkylacrylate) wherein said poly(n-alkylacrylate) is initially introduced in said residual fuel at a temperature above the solution point of said wax.
  • This invention relates to a novel interpolymeric poly(n-alkylacrylate) pour depressor, to wax containing residual fuel oil compositions of reduced pour point containing said pour depressor and to making greater utilization of low sulfur, high wax content residual fuel oils.
  • pour points of the order of about 50F. and less, preferably less than 30F are required. This reduction in pour point is often accomplished through the use of pour depressors.
  • many of the pour depressors which are effective in non-waxy fuels for example, copolymers of dodccyl and octadecyl methacrylates and interpolymeric polymers of alkyl acrylatcs wherein a substantial portion of the alkyl groups, i.c., greater than about 35%, containing more than 24 and less than 20 carbons and/or are branched chain are relatively ineffective
  • there is a continuing need in this area for the finding of low cost pour depressors that are significantly effective in lowering the pour point of high pour waxy residual fuels.
  • the interpolymeric poly(n-alkylacrylates) contemplated herein are of a molecular weight between about 3000 and 100,000, preferably between 4000 and 52,000, most preferably between 15,000 and 35,000, said alkyl being of at least 18 carbons and at least 70 wt. 7( of said alkyl is between 20 to 24 carbons inclusively, the C to C alkyl group consisting of between about 2 and 65 wt. 71 C21, alkyl, between about 18 and 65 wt. "/1 C alkyl, and between about 8 and 35 wt. 7: C alkyl.
  • the interpolymers are derived from standard polymerization techniques such as polymerizing the alkyl acrylate monomers in the presence of acrylate polymerization catalyst. e.g., azo catalysts such as azobisisobutronitrile of US; Pat. No. 2,471,959 or the well known peroxide catalysts such as benzoyl peroxide and lauroyl peroxide utilizing catalyst quantities of between about 0.1 and 5 wt.
  • Polymerization is normally conducted at a temperature between about 50 and 150F., preferably at to C., utilizing a nitrogen blanket to prevent oxidation and azobisisobutronitrile catalyst.
  • periodic sampling is taken for refractive index (RI) determination.
  • the polymerization reaction is continued until the refractive index remains relatively steady.
  • the reaction time is normally between about 1 and 10 hours.
  • n-alkylacrylate monomers from which the poly(n-alkylacrylate) interpolymeric products are derived are prepared by standard esterification techniques through the reaction of acrylic acid with n-alkanol mixtures wherein the reactive nalkanols in said mixtures have at least 18 carbons and at least about 70 wt. of the n-alkanol portion is of from 20 to 24 carbon atoms, the C to C group consisting of between about 2 and 65 wt. eicosanol, between about 18 and 65 wt docosanol, and between about 8 and 35 wt. 7: tetracosanol.
  • Alfolsl are impure mixtures containing as the major portion, i.c., greater than 50 wt. 7:- n-alkanols of various chain lengths, the remainder consisting of hydrocarbon, ketones and hindered unreactive alcohols.
  • Typical analysis of two suitable examples of the Alfol alcohols are as follows:
  • alcohol as defined to produce the polyacrylate with the n-alkyl group ranges as set forth in material to the effectiveness of the pour depressor in the waxy residuum compositions contemplated herein. If the alcohol employed is not within the contemplated chain lengths and/or of substantial branch chain strucutre, polyacrylates are produced outside the defined limitations and are either ineffective or relatively ineffective in depressing the pour of the defined waxy fuels.
  • a standard means of acrylate monomer precursor preparation is reacting (csterifying) the alcohol mix ture with acrylic acid in the presence of an esterification catalyst such as p-toluenesulfonic acid and a polymerization inhibitor, e.g., hydroquinone, desirably in the presence of an azeotroping agent for water byproduct removal such as benzene.
  • the esterification is conducted, for example, at a temperature of between about and 200F. and is continued until the amount of water by-product is removed as overhead indicates that the esterification is essentially complete.
  • the wax containing residual heavy fuel oil bases contemplated herein contain a percentage of residual components as opposed to no residual components in distillate fuels.
  • the contemplated petroleum residual components normally have a pour point up to lOOF. or more and macrocrystalline paraffin wax content of the order of between 4 and 35 wt.
  • the amount of residual components in the base fuel compositions contemplated herein may vary in wide limits, e.g., up to 100 volume but are normally between about 25 and 75 volume of the total fuel quantity.
  • the residual components may be obtained as a residue in the distillation of crude oil at temperatures between about 400 and 1050F.
  • cutter stocks are present in sufficient quantities to insure a macrocrystalline paraffin wax content in the final product of between 4 and 15 wt. preferably between 5 and wt. /0.
  • the cutter stocks normally constitute between about and 75 volume 70 of the final composition.
  • the concentration in which the polyacrylates are incorporated in the waxy residual fuel oil base will be widely varied since it is dependent on the nature and the quality of the residual fuel oil and the degree of pour depressing required. Pour depressing effect is sometimes evidenced in amounts as small as about 0.01 wt. and quantities up to 2 wt. are usually sufficient.
  • the waxy residual fuel oils contain between about 0.04 and 0.5 wt. polyacrylates.
  • the polyacrylate may be diluted with a solvent such as light gas oil of a kinematic viscosity (es) of between about 2 and 4 at 100F. to form a between about 10 and 50 wt. 70 polyacrylate gas oil concentrate.
  • the polyacrylate pour depressor be introduced into the residual fuel at a temperature above the solution point of the macrocrystalline paraffin wax component. Usually, a temperature of about 200F. or more is required. If the polyacrylate is contacted with the wax component at a temperature substantially below the solution point of a substantial portion of the wax, there is little or no pour dcpressing effect afforded by the polyacrylate.
  • the polyacrylate is preferably first mixed with the cutter stock, desirably at an elevated temperature, e.g., between about 100 and 150F. and the polyacrylate-distillate mixture is in turn mixed with the wax containing residuum fuel component at a temperature above the solution point of the wax component, e.g., 200F.
  • the poly( alkylacrylate) may be blended in the waxy residual base fuel in its entirety at a temperature above the solution point of the wax component followed by the addition of the cutter stock.
  • EXAMPLE I This example illustrates the manufacture of the poly( n-alkylacrylate) pour point depressors.
  • Monomeric alkyl acrylate of three alcohols were prepared. Alcohols A and B are within the scope of the invention and Alcohol C is included for comparative purposes. These alcohols were of the following compositions:
  • Alcohol Alcohol Alcohol Typical Properties A B C Approx. homolog distribution 100% alcohol basis, wt. 71
  • Polyacrylate-Oil Concentrate The resultant polyacrylatc products were diluted 5 with a light hydrocarbon oil having a pour point of about F. and a kinematic viscosity at 100F. of about 3 to form a 25 wt. 7: concentrate solution of the polyacrylate. 5
  • the fuel oil employed was a heavy waxy residual fuel oil comprising 50 vol. macrocrystalline wax containing vacuum petroleum residuum and 50 vol. nonwaxy hydrotreated gas oil having a boiling point of between about 400-652F., an API gravity of 35.3 and a pour point of about 5F.
  • the resultant base fuel composition had the following properties:
  • the petroleum vacuum residuum component was heated to 200F. with stirring for V2 hour during which time the polyacrylates prepared in Example I were added. Subsequently, the hydrotreated gas oil was blended into the mixture at 150F. followed by stirring at 155F. for an additional 0.5 hour.
  • the effectiveness of the three polyacrylates (PAA) representative A and B, comparative C) produced in Example I in depressing the pour point of the waxy residual fuel is set forth below in the following table:
  • the waxy residual base fuel (BF) was that described in Example 11 and the polyacrylate (PAA) was the Poly-Acrylate A prepared in Example 1.
  • Two blending runs were made. Run 1 representative of the invention and Run 2 is a comparative blending technique.
  • Poly-Methacrylate D is and results are re orted below: a co ol mer of laur l and octadec l methacr late co- P P y y y y polymerized in a weight ratio of 4:1 and having an ino trinsic viscosity in benzene at 77F. of about 0.58.
  • the Dcsmpm" test data and results are reported below:
  • This residue has alkylatcrylatc') of a molepular we'lght a a wax content of 16 8 wt
  • the n-dlkyl ls of at least 18 was designated as i 6 is a 650+F (atm p carbons and at least 70 wt. of said n-alkyl is of 20 to sure) residuum of an Arabian crude oil which is a mac- 24 carbons Consisting of between about 2 2 3 E' .Q e 18a 6 wak rocrystallme paraffin wax content of about 2 wt.
  • g lkyl beg/e :i y
  • the third blend tested is a 60/40 volume "/0 blend of ween 3 Y 0 y BF 4 and 3R6 which are the y residual heavy fuel ly(n-alkylacrylatc) introduced into said 011 at a temperth l d w 01] bases contemplated herein having a wax content of g i ggg i i zz gg g jg 52 claim 1 wherein a o 5 21121 55 232; gg ig i i g' ggf gg said residual fuel oil consists of between about 25 and of the invention.
  • BF-4 and BF-6 fuels are individually 75 Y i petlroleum residuum hat/Inga f outside of said sco e
  • the test data and results are re- Crystalline pdmffin wax content between about 15 and t d b low p 35 wt. 7: and between about 25 and 75 volume 7r of a per 0 c cutter stock seleeted from the group consisting of a petroleum residuum having a macrocrystallinc paraffin Blend point 40 wax content between about land 10 wt. "/1 and a nonwax containing petroleum distillate having a boiling 35:: point between 300 and 850F. g 60 vol. "/1 BF-4/l3F-6 s5 3.
  • the base fuel (BF) was that described in Example ll.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US250900A 1972-05-08 1972-05-08 Polyacrylates and waxy residual fuel compositions thereof Expired - Lifetime US3904385A (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
US250900A US3904385A (en) 1972-05-08 1972-05-08 Polyacrylates and waxy residual fuel compositions thereof
DE2264328A DE2264328A1 (de) 1972-05-08 1972-12-30 Poly(n-alkylacrylat) und seine verwendung als stockpunkterniedriger in einer schweren erdoelfraktion
AR247454A AR208270A1 (es) 1972-05-08 1973-01-01 Un poli(acrilato de n-alquilo)interpolimerico
ZA731515A ZA731515B (en) 1972-05-08 1973-03-05 Polyacrylates and waxy residual fuel compositions
GB1126873A GB1368729A (en) 1972-05-08 1973-03-08 Polyacrylates and waxy residual fuel compositions
AU53306/73A AU466151B2 (en) 1972-05-08 1973-03-15 Polyacrylates and waxy residual fuel compositions
CA166,623A CA992697A (en) 1972-05-08 1973-03-21 Polyacrylates and waxy residual fuel compositions thereof
CA166,621A CA1020533A (en) 1972-05-08 1973-03-21 Wax containing crude oil compositions of reduced pour point
CA166,624A CA1020534A (en) 1972-05-08 1973-03-21 Waxy residual lube oil composition of reduced pour point
NL7303927A NL7303927A (xx) 1972-05-08 1973-03-21
CA166,622A CA987492A (en) 1972-05-08 1973-03-21 Vacuum gas oils comprising interpoly (n-alkylacrylates)
AT254673A AT329170B (de) 1972-05-08 1973-03-22 Stockpunkterniedriger
CH438973A CH582232A5 (xx) 1972-05-08 1973-03-27
SE7304294A SE396403B (sv) 1972-05-08 1973-03-27 Komposition innehallande en vaxhaltig, tjock petroleumfraktion eller en vaxhaltig raolja och en flytpunktssenkande mengd av ett sampolymert poly(n-alkylakrylat) samt sett att framstella densamma
NO1282/73A NO137864C (no) 1972-05-08 1973-03-28 Oljeblanding omfattende en voksholdig tung petroleumfraksjon og inneholdende makrokrystallinsk parafinvoks
FR7314133A FR2190850B1 (xx) 1972-05-08 1973-04-18
BE130233A BE798484A (fr) 1972-05-08 1973-04-19 Polyacrylates de n-alkyle abaissant le point d'ecoulement des fractions de petrole contenant des paraffines
JP48045230A JPS4926303A (xx) 1972-05-08 1973-04-23
BR324573A BR7303245D0 (pt) 1972-05-08 1973-05-04 Novos poli-(acrilatos de n-alquila), composicoes contendo os mesmos como depressores do ponto de fluidez, e processo para preparar essas composicoes
IT23828/73A IT987198B (it) 1972-05-08 1973-05-08 Riduttore del punto di scorri mento e composizione di frazio ni di petrolio pesanti cerose che lo contengono
ES414436A ES414436A1 (es) 1972-05-08 1973-05-18 Un metodo de reduccion del punto de fluidez de una fraccionpesada de petroleo que contiene parafina.
US05/553,182 US3951929A (en) 1972-05-08 1975-02-26 Polyacrylates and waxy residual fuel compositions thereof

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US25148572A 1972-05-08 1972-05-08
US25163872A 1972-05-08 1972-05-08
US250900A US3904385A (en) 1972-05-08 1972-05-08 Polyacrylates and waxy residual fuel compositions thereof
US26683972A 1972-06-27 1972-06-27
US05/553,182 US3951929A (en) 1972-05-08 1975-02-26 Polyacrylates and waxy residual fuel compositions thereof

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US05/553,182 Division US3951929A (en) 1972-05-08 1975-02-26 Polyacrylates and waxy residual fuel compositions thereof

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US3904385A true US3904385A (en) 1975-09-09

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US250900A Expired - Lifetime US3904385A (en) 1972-05-08 1972-05-08 Polyacrylates and waxy residual fuel compositions thereof
US05/553,182 Expired - Lifetime US3951929A (en) 1972-05-08 1975-02-26 Polyacrylates and waxy residual fuel compositions thereof

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US05/553,182 Expired - Lifetime US3951929A (en) 1972-05-08 1975-02-26 Polyacrylates and waxy residual fuel compositions thereof

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US (2) US3904385A (xx)
AT (1) AT329170B (xx)
BE (1) BE798484A (xx)
CA (4) CA1020534A (xx)
CH (1) CH582232A5 (xx)
DE (1) DE2264328A1 (xx)
FR (1) FR2190850B1 (xx)
GB (1) GB1368729A (xx)
NL (1) NL7303927A (xx)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4668733A (en) * 1985-03-29 1987-05-26 Henkel Kommanditgesellschaft Auf Aktien Pour point depressants comprising polyolefins modified with side chains
US4728414A (en) * 1986-11-21 1988-03-01 Exxon Research And Engineering Company Solvent dewaxing using combination poly (n-C24) alkylmethacrylate-poly (C8 -C20 alkyl (meth-) acrylate dewaxing aid
US4862908A (en) * 1986-07-17 1989-09-05 Ruhrchemie Aktiengesellschaft Mineral oils and mineral oil distillates having improved flowability and method for producing same
DE3807395A1 (de) * 1988-03-07 1989-09-21 Henkel Kgaa Verwendung ausgewaehlter copolymertypen der acryl- und/oder methacrylsaeureester als fliessverbesserer in paraffinreichen erdoelen und erdoelfraktionen (ii)
US4906682A (en) * 1986-04-19 1990-03-06 Rohm Gmbh Ethylene-vinyl ester copolymer emulsions
US5281329A (en) * 1989-07-14 1994-01-25 Rohm Gmbh Method for improving the pour point of petroleum oils
US5349019A (en) * 1988-12-24 1994-09-20 Hoechst New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils
US5718821A (en) * 1991-07-18 1998-02-17 Hoechst Aktiengesellschaft Copolymers of ethylenically unsaturated carboxylic acid esters with polyoxyalkylene ethers of lower, unsaturated alcohols as flow-improving agents for paraffin containing oils
US20030041508A1 (en) * 1999-12-23 2003-03-06 Sheetal Handa Polyacrylate esters, their preparation and use as a low-temperature flow-improver in middle distillate oils
US20060003903A1 (en) * 2004-07-05 2006-01-05 Ooi Tian L Process for producing oligomers
US20090173080A1 (en) * 2008-01-07 2009-07-09 Paul Steven Wallace Method and apparatus to facilitate substitute natural gas production

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4146492A (en) * 1976-04-02 1979-03-27 Texaco Inc. Lubricant compositions which exhibit low degree of haze and methods of preparing same
US4071678A (en) * 1976-04-29 1978-01-31 The United States Of America As Represented By The Secretary Of The Army Random copolymers of methyl methacrylate and N-octadecyl methacrylate
DE2926474C2 (de) * 1979-06-30 1984-08-30 Chemische Fabriek Servo B.V., Delden Acrylester-Mischpolymerisate und ihre Verwendung als Kristallisationsinhibitoren für paraffinhaltige Rohöle
DE3513356A1 (de) * 1985-04-15 1986-10-16 Henkel KGaA, 4000 Düsseldorf Neue ester ungesaettigter polymerisierbarer carbonsaeuren, daraus gewonnene oelloesliche homo- und copolymere, verfahren zu ihrer herstellung und ihre verwendung als stockpunktserniedriger
DE3544061A1 (de) * 1985-12-13 1987-06-19 Roehm Gmbh Hochscherstabile mehrbereichsschmieroele mit verbessertem viskositaetsindex
DE3607444A1 (de) * 1986-03-07 1987-09-10 Roehm Gmbh Additive fuer mineraloele mit stockpunktverbessernder wirkung
DE3807394A1 (de) * 1988-03-07 1989-09-21 Henkel Kgaa Verwendung ausgewaehlter copolymertypen der acryl- und/oder methacrylsaeureester als fliessverbesserer in paraffinreichen erdoelen und erdoelfraktionen (i)
DE3818438A1 (de) * 1988-05-31 1989-12-07 Roehm Gmbh Mineraloele mit verbessertem fliessverhalten
DE3830913A1 (de) * 1988-09-10 1990-03-15 Henkel Kgaa Neue waessrige emulsionscopolymerisate, insbesondere in wasser- und oel-verduennbarer form zur verbesserung der fliesseigenschaften und stockpunktserniedrigung von erdoelen und erdoelfraktionen sowie ihre verwendung
US5312884A (en) * 1993-04-30 1994-05-17 Rohm And Haas Company Copolymer useful as a pour point depressant for a lubricating oil
CN1063218C (zh) * 1995-11-29 2001-03-14 鲁布里佐尔公司 蜡状倾点下降剂的分散体
US5851429A (en) * 1996-04-08 1998-12-22 The Lubrizol Corporation Dispersions of waxy pour point depressants
FR2746400B1 (fr) * 1996-03-21 1998-04-24 Ceca Sa Homopolymeres et copolymeres acryliques comme additifs pour l'inhibition du depot de paraffines dans les huiles brutes et compositions renfermant les huiles et lesdits additifs
MX2013014352A (es) 2013-12-06 2015-06-10 Inst Mexicano Del Petróleo Formulaciones de homopolimeros base acrilatos de alquilo empleadas como antiespumantes en aceites crudos pesados y super-pesados.
MX2015009234A (es) 2015-07-17 2017-01-16 Inst Mexicano Del Petróleo Formulaciones de copolimeros base acrilatos de alquilo empleadas como antiespumantes en aceites crudos pesados y super-pesados.
MX2016004130A (es) 2016-03-31 2017-09-29 Inst Mexicano Del Petróleo Formulaciones de terpolimeros base acrilatos de alquilo empleadas como antiespumantes en aceites crudos gasificados pesados y super-pesados.
WO2017182574A1 (de) 2016-04-21 2017-10-26 Universität Hamburg Rohölzusammensetzung, umfassend ein additiv zur verbesserung der fliesseigenschaften von paraffinhaltigem rohöl

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US4668733A (en) * 1985-03-29 1987-05-26 Henkel Kommanditgesellschaft Auf Aktien Pour point depressants comprising polyolefins modified with side chains
US4906682A (en) * 1986-04-19 1990-03-06 Rohm Gmbh Ethylene-vinyl ester copolymer emulsions
US4862908A (en) * 1986-07-17 1989-09-05 Ruhrchemie Aktiengesellschaft Mineral oils and mineral oil distillates having improved flowability and method for producing same
US4728414A (en) * 1986-11-21 1988-03-01 Exxon Research And Engineering Company Solvent dewaxing using combination poly (n-C24) alkylmethacrylate-poly (C8 -C20 alkyl (meth-) acrylate dewaxing aid
DE3807395A1 (de) * 1988-03-07 1989-09-21 Henkel Kgaa Verwendung ausgewaehlter copolymertypen der acryl- und/oder methacrylsaeureester als fliessverbesserer in paraffinreichen erdoelen und erdoelfraktionen (ii)
US5039432A (en) * 1988-03-07 1991-08-13 Henkel Kommanditgesellschaft Auf Aktien Copolymers of (meth) acrylic acid esters as flow improvers in oils
US5349019A (en) * 1988-12-24 1994-09-20 Hoechst New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils
US5281329A (en) * 1989-07-14 1994-01-25 Rohm Gmbh Method for improving the pour point of petroleum oils
US5718821A (en) * 1991-07-18 1998-02-17 Hoechst Aktiengesellschaft Copolymers of ethylenically unsaturated carboxylic acid esters with polyoxyalkylene ethers of lower, unsaturated alcohols as flow-improving agents for paraffin containing oils
US20030041508A1 (en) * 1999-12-23 2003-03-06 Sheetal Handa Polyacrylate esters, their preparation and use as a low-temperature flow-improver in middle distillate oils
US20060003903A1 (en) * 2004-07-05 2006-01-05 Ooi Tian L Process for producing oligomers
US8507424B2 (en) * 2004-07-05 2013-08-13 Malaysian Palm Oil Board Process for producing oligomers
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DE2264328A1 (de) 1973-11-29
NL7303927A (xx) 1973-11-12
CA1020534A (en) 1977-11-08
US3951929A (en) 1976-04-20
FR2190850A1 (xx) 1974-02-01
ATA254673A (de) 1975-07-15
GB1368729A (en) 1974-10-02
FR2190850B1 (xx) 1976-03-05
AU5330673A (en) 1974-09-19
AT329170B (de) 1976-04-26
BE798484A (fr) 1973-10-19
CA992697A (en) 1976-07-06
CA987492A (en) 1976-04-20
CA1020533A (en) 1977-11-08
CH582232A5 (xx) 1976-11-30

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