CN108431185A - Fatty acid methyl ester composition with low pour point - Google Patents

Fatty acid methyl ester composition with low pour point Download PDF

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Publication number
CN108431185A
CN108431185A CN201680075215.7A CN201680075215A CN108431185A CN 108431185 A CN108431185 A CN 108431185A CN 201680075215 A CN201680075215 A CN 201680075215A CN 108431185 A CN108431185 A CN 108431185A
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CN
China
Prior art keywords
composition
pour point
equal
fatty acid
oil
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Pending
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CN201680075215.7A
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Chinese (zh)
Inventor
S.勒布伦
O.佐维
S.德普雷特
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Arkema France SA
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Arkema France SA
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Publication of CN108431185A publication Critical patent/CN108431185A/en
Pending legal-status Critical Current

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    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • 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
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • 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
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C10M2207/2895—Partial esters containing free hydroxy groups used as base material
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to include composition below：At least Castor Oil Fatty Acid mixtures of methyl esters of 95 weight %；Reduce the additive of pour point；The maximum pour point of composition is 0 DEG C.Purposes the invention further relates to the composition as lubricant, concrete parting agent, degreasing agent or detergent.

Description

Fatty acid methyl ester composition with low pour point
Technical field
The present invention relates to the compositions based on the fatty acid methyl ester derived from castor oil, with low pour point.The composition It is especially used as lubricant or the demoulding for promoting concrete.
Background technology
Known plant or animal oil (it is the mixture of different aliphatic acid) carrying out transesterification with generate for example for The product of lubrication.
The aliphatic acid composition of each plant or animal oil and other plant oil or animal oil is widely different, so that each ester It exchanges oil and all has different property.
Particularly useful product, especially as lubricant or the product as concrete parting agent is to be derived from castor oil Fatty acid methyl ester mixture.The product mainly contains C11-C22 fatty acid methyl esters, principle example be methyl linoleate and Methyl oleate.The product special compound also containing there are two types of, does not see in the product derived from other plant oil usually, i.e., Shiyixisuan Undecylenic Acid and methyl ricinoleate.
The product is especially by Arkema with titleEsterol A sale.However, one of the product the disadvantage is that It is with relatively high pour point, at+6 DEG C or so (according to standard ASTM D97).Due to this reason, make in arctic weather It is highly difficult with the product.
The known pour point that the various products derived from plant or animal oil are reduced using pour point depressor additive.
Therefore, document EP 0543356, EP 0626442, US 6,409,778, US 6,051,538 and US 2011/ 296743 describe the various compositions for wherein using pour point depressor additive.
But in general, it is dropped in order to use the product derived from plant or animal oil in arctic weather The possibility of the low product pour point depends on the property and characteristic of the product.It is therefore desirable to be able to improve derived from castor oil The mixture of fatty acid methyl ester allows it to use in arctic weather.
Invention content
Present invention firstly relates to include composition below：
At least mixture of the Castor Oil Fatty Acid methyl esters of 95 weight %；
Pour point depressor (depressant) additive；
The pour point of composition is less than or equal to 0 DEG C.
According to an embodiment, the pour point of composition is less than or equal to -5 DEG C, preferably lower than or equal to -9 DEG C.
According to an embodiment, the iodine number of the mixture of Castor Oil Fatty Acid methyl esters be 100 to 120g/100g and with Weight ratio meter includes：
- 5 to 20%, preferably 8 to 12% methyl stearate；
- 20 to 40%, preferably 25 to 35% methyl oleate；
- 30 to 50%, preferably 35 to 45% methyl linoleate；
It is less than 10%, preferably smaller than 8.5% methyl hexadecanoate；
- 1.5 to 4%, preferably 2 to 3% methyl ricinoleate；
- 0.4 to 1.5%, preferably 0.6 to 1% Shiyixisuan Undecylenic Acid.
According to an embodiment, composition includes that the pour point of 1 to 2%, preferably 1.2 to 1.8% weight ratio inhibits Agent addition agent.
According to an embodiment, pour point depressor additive is dissolved in acrylic polymer (the preferably root in oil General formula shown in lower according to this), ratio is preferably the oil of 60 to 100 parts of acrylic polymer/15 to 40 part.
According to an embodiment, which is paraffin distillate.
According to an embodiment, additive has：
According to 200 to 500mm at 100 DEG C of standard ASTM D4452/ s, preferably 300 to 400mm2The viscosity of/s；
According to the pour point for being less than or equal to -30 DEG C, preferably lower than or equal to -36 DEG C of standard ASTM D97；
It is less than or equal to 0.6mg's KOH/g, preferably lower than or equal to 0.5mg KOH/g according to standard ASTM D974 Acid value.
Purposes the invention further relates to combination of the above object as lubricant, concrete parting agent, degreasing agent or detergent.
The invention enables can overcome the prior art.It more particularly provides the aliphatic acid derived from castor oil The mixture of methyl esters can use in arctic weather.
This by using the pour point of mixture can be reduced (inhibit, depress) to less than 0 DEG C, preferably shorter than -5 DEG C or Additive less than -9 DEG C is realized.
Description of the drawings
Fig. 1 shows the crystallization kineticses of various compositions, by being formed by the thickness of crystal layer (on the y axis, with mm Meter) estimate as the function of temperature (in x-axis, by DEG C in terms of).Details are described in following example 1.
Specific implementation mode
The in more detail and in a non limiting manner description present invention in the following description now.
Composition according to the present invention will be by that will be derived from the mixture and pour point depressor of the fatty acid methyl ester of castor oil Additive is mixed and is obtained.
The mixture of fatty acid methyl ester derived from castor oil is obtained by the transesterification of castor oil and methanol.Mixture Transesterification degree is not necessarily 100%, it means that the conjunction object that the methyl esters discussed mixes can include a certain proportion of non-esterified fat Fat acid.
The mixture of fatty acid methyl ester derived from castor oil is preferably characterized in that, according to the pour point of standard ASTM D97 It is 5 to 8 DEG C；And/or iodine number is 100 to 120g/100g.Iodine number can be measured according to standard ISO 3961.
The mixture of the fatty acid methyl ester discussed preferably comprises：
- 5 to 20%, preferably 8 to 12% methyl stearate (C18:0)；
- 20 to 40%, preferably 25 to 35% methyl oleate (C18:1)；
- 30 to 50%, preferably 35 to 45% methyl linoleate (C18:2)；
It is less than 10%, preferably smaller than 8.5% methyl hexadecanoate (C16:0)；
- 1.5 to 4%, preferably 2 to 3% methyl ricinoleate (C18:1(OH))；
- 0.4 to 1.5%, preferably 0.6 to 1% Shiyixisuan Undecylenic Acid (C11:1).
Pour point depressor additive is selected, so that can 0 be decreased below the pour point of composition according to the present invention DEG C (preferably shorter than -1 DEG C, or -2 DEG C, or -3 DEG C, or -4 DEG C, or -5 DEG C, or -6 DEG C, or -7 DEG C, or -8 DEG C, or -9 DEG C, according to Standard ASTM D97).
Its acrylic polymer that can be especially dissolved in oil (it includes acrylic copolymer).Relative scale The preferably oil of 60 to 100 parts of acrylic polymer/15 to 40 part.
Acrylic polymer is preferably the polyalkyl methacrylate of following general formula：
Wherein n is preferably 200 to 2000 integer, and each R independently indicates C1 to C22 alkyl.
Oil can be obtained for example by the catalytic hydrogenation of petroleum distillate, and include mainly C15 to the C30 hydrocarbon being mainly saturated And the viscosity at 40 DEG C is less than 19cSt.It can especially have the oil of label CAS64742-55-8.
Oil can also be obtained by the catalytic hydrogenation of petroleum distillate, and include mainly C20 to the C30 hydrocarbon that is mainly saturated simultaneously And the viscosity at 40 DEG C is more than 19cSt.It can especially have the oil of label CAS64742-54-7.
Oil can also be obtained by petroleum distillate by crystallizing in a solvent except deparaffnize, and include mainly C20 to C30 Hydrocarbon and viscosity at 40 DEG C is more than 19cSt.It can especially have the oil of label CAS64742-65-0.
The mixture of above oil can also be used.
Additive preferably has：
According to 200 to 500mm at 100 DEG C of standard ASTM D4452/ s, preferably 300 to 400mm2The viscosity of/s； And/or
It is less than or equal to -30 DEG C, preferably lower than or equal to -36 DEG C of pour points according to standard ASTM D97；
It is less than or equal to 0.6mg's KOH/g, preferably lower than or equal to 0.5mg KOH/g according to standard ASTM D974 Acid value.
Specially suitable additive is by Evonik to markThe product of 1-211 sale.
Additive can be present in the weight ratio of 0.1 to 5% and preferably 1 to 2% in composition.Preferred content model Enclosing is：1.0 to 1.1%；1.1 to 1.2%；1.2 to 1.3%；1.3 to 1.4%；1.4 to 1.5%；1.5 to 1.6%；1.6 extremely 1.7%；1.7% to 1.8%；1.8 to 1.9% and 1.9 to 2.0%.It is specially suitable that weight content, which is about 1.5%,.
The content of acrylic copolymer or polymer in the composition of the present invention is preferably 0.5 to 2%, more preferably 0.8 to 1.4% (especially 0.8 to 0.9% or 0.9 to 1.0% or 1.0 to 1.1% or 1.1 to 1.2% or 1.2 to 1.3% or 1.3 to 1.4%).
According to an embodiment, composition is substantially by the mixture and pour point of the fatty acid methyl ester derived from castor oil Inhibitor additive forms.According to another embodiment, composition by the fatty acid methyl ester derived from castor oil mixture It is formed with pour point depressor additive.
Embodiment
Following example illustrate the present invention rather than it is limited.
Embodiment 1
Various pour point depressor additives are added to by Arkema with 1 to 2.5% amount with title Mixture (the pour point of the fatty acid methyl ester derived from castor oil of Esterol A sale：+ 6 DEG C) in.
Used additive is as follows：
-10-310(Evonik)：Acrylic copolymer of the amount more than or equal to 60%, with dish Seed oil combines, and the viscosity at 100 DEG C is 1800mm2/s；
-1-211(Evonik)：Acrylic polymer of the amount more than or equal to 60%, with neutrality Oil combines, and the viscosity at 100 DEG C is 400mm2/s；
-1-180(Evonik)：The acrylic copolymer that amount is 40 to 70%, with neutral oil knot It closes, the viscosity at 100 DEG C is 300mm2/s；
-1-255(Evonik)：The acrylic copolymer that amount is 15 to 40%, with neutral oil knot It closes, the viscosity at 100 DEG C is 45mm2/s。
The pour point of the composition obtained by this method is summarized in following table：
Pour point (ASTM D97)
It has been observed that additive1-211 is particularly advantageous, because it allows to a concentration of Pour point is reduced to -9 DEG C under only 1.5%.
In addition, the thickness (packed height 55mm) by measuring the crystal layer formed in keeping sample in test tube, The measurement of crystallization kinetics is carried out between 5 and -3 DEG C.These measurements are related to prepared with 1.5% above four kinds of additives four Kind composition, and further relate toThe control sample of Esterol A.As a result shown in Figure 1.Which demonstrate additives1-211 provides most slow crystallization kinetics.
Curve 1 indicates that the reference composition of not additive, curve 2 indicate to usePrepared by 1-255 Composition, curve 3 indicate to useComposition prepared by 1-180, curve 4 indicate to use Composition prepared by 10-310, and curve 5 indicates to useComposition prepared by 1-211.
Embodiment 2
After being stored 7 days at -7 DEG C in a static condition, various groups of assessment product preparation in the same manner as in Example 1 Close the consistency of object.
As a result it is shown in following table：
The uniformity and mobility of product
WithThe composition that 1-211 is obtained is best in terms of uniformity and mobility, because The content of additive keeps moderate (1.5%).

Claims (9)

1. including composition below：
At least mixture of the Castor Oil Fatty Acid methyl esters of 95 weight %；
Pour point depressor additive；
The pour point of composition is less than or equal to 0 DEG C.
2. composition as described in claim 1, pour point is less than or equal to -5 DEG C, preferably lower than or equal to -9 DEG C.
3. composition as claimed in claim 1 or 2, the wherein iodine number of the mixture of Castor Oil Fatty Acid methyl esters be 100 to 120g/100g and include in terms of weight ratio：
- 5 to 20%, preferably 8 to 12% methyl stearate；
- 20 to 40%, preferably 25 to 35% methyl oleate；
- 30 to 50%, preferably 35 to 45% methyl linoleate；
It is less than 10%, preferably smaller than 8.5% methyl hexadecanoate；
- 1.5 to 4%, preferably 2 to 3% methyl ricinoleate；
- 0.4 to 1.5%, preferably 0.6 to 1% Shiyixisuan Undecylenic Acid.
4. the composition as described in one in claims 1 to 3, it includes 1 to 2%, preferably 1.2 to 1.8% weight ratio Pour point depressor additive.
5. the composition as described in one in Claims 1-4, wherein pour point depressor additive are dissolved in the propylene in oil Acids polymers, ratio are preferably the oil of 60 to 100 parts of acrylic polymer/15 to 40 part.
6. composition as claimed in claim 5, wherein acrylic polymer have following formula：
Wherein n is preferably 200 to 2000 integer, and each R indicates C1 to C22 alkyl.
7. such as composition described in claim 5 or 6, wherein oil is paraffin distillate.
8. the composition as described in one in claim 1 to 7, wherein additive have：
According to 200 to 500mm at 100 DEG C of standard ASTM D4452/ s, preferably 300 to 400mm2The viscosity of/s；
According to the pour point for being less than or equal to -30 DEG C, preferably lower than or equal to -36 DEG C of standard ASTM D97；
According to the acid for being less than or equal to 0.6mg KOH/g, preferably lower than or equal to 0.5mg KOH/g of standard ASTM D974 Value.
9. the composition as described in one in claim 1 to 8 is as lubricant, concrete parting agent, degreasing agent or detergent Purposes.
CN201680075215.7A 2015-12-21 2016-12-21 Fatty acid methyl ester composition with low pour point Pending CN108431185A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1562926A FR3045660B1 (en) 2015-12-21 2015-12-21 COMPOSITION OF METHYL ESTERS OF LOW POUR POINT FATTY ACIDS
FR1562926 2015-12-21
PCT/FR2016/053611 WO2017109411A1 (en) 2015-12-21 2016-12-21 Fatty acid methyl ester composition having a low pour point

Publications (1)

Publication Number Publication Date
CN108431185A true CN108431185A (en) 2018-08-21

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Country Status (7)

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EP (1) EP3394228A1 (en)
KR (1) KR20180094097A (en)
CN (1) CN108431185A (en)
FR (1) FR3045660B1 (en)
MY (1) MY197228A (en)
SG (1) SG11201805309VA (en)
WO (1) WO2017109411A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110699195A (en) * 2019-09-30 2020-01-17 义乌欧风汽车用品有限公司 Degumming composition and preparation method and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2331761A (en) * 1999-03-15 1999-06-02 Procter & Gamble Pour point depression of heavy cut methyl esters via alkyl methacrylate copolymer
CN1221002A (en) * 1997-10-24 1999-06-30 乙基公司 Novel pour point depressants via anionic polymerization of (mesh) acrylic monomers
US6051538A (en) * 1999-01-26 2000-04-18 The Procter & Gamble Company Pour point depression of heavy cut methyl esters via alkyl methacrylate copolymer
JP2004149705A (en) * 2002-10-31 2004-05-27 Lion Corp Higher fatty acid ester-based solvent and viscosity-reducing agent for foaming polyurethane
CN1572862A (en) * 2003-06-23 2005-02-02 英菲诺姆国际有限公司 Oil compositions
CN102282242A (en) * 2009-01-13 2011-12-14 赢创罗曼克斯添加剂有限公司 Fuel compositions having improved cloud point and improved storage properties

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1221002A (en) * 1997-10-24 1999-06-30 乙基公司 Novel pour point depressants via anionic polymerization of (mesh) acrylic monomers
US6203585B1 (en) * 1998-03-02 2001-03-20 The Procter & Gamble Company Pour point depression of heavy cut methyl esters via alkyl methacrylate copolymer
US6051538A (en) * 1999-01-26 2000-04-18 The Procter & Gamble Company Pour point depression of heavy cut methyl esters via alkyl methacrylate copolymer
GB2331761A (en) * 1999-03-15 1999-06-02 Procter & Gamble Pour point depression of heavy cut methyl esters via alkyl methacrylate copolymer
JP2004149705A (en) * 2002-10-31 2004-05-27 Lion Corp Higher fatty acid ester-based solvent and viscosity-reducing agent for foaming polyurethane
CN1572862A (en) * 2003-06-23 2005-02-02 英菲诺姆国际有限公司 Oil compositions
CN102282242A (en) * 2009-01-13 2011-12-14 赢创罗曼克斯添加剂有限公司 Fuel compositions having improved cloud point and improved storage properties

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110699195A (en) * 2019-09-30 2020-01-17 义乌欧风汽车用品有限公司 Degumming composition and preparation method and application thereof
CN110699195B (en) * 2019-09-30 2021-08-17 义乌欧风汽车用品有限公司 Degumming composition and preparation method and application thereof

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KR20180094097A (en) 2018-08-22
FR3045660A1 (en) 2017-06-23
WO2017109411A1 (en) 2017-06-29
EP3394228A1 (en) 2018-10-31
FR3045660B1 (en) 2020-08-21
SG11201805309VA (en) 2018-07-30
MY197228A (en) 2023-06-06

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