WO2023031417A1 - Composition lubrifiante présentant des propriétés d'épaississement à froid améliorées - Google Patents
Composition lubrifiante présentant des propriétés d'épaississement à froid améliorées Download PDFInfo
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- WO2023031417A1 WO2023031417A1 PCT/EP2022/074489 EP2022074489W WO2023031417A1 WO 2023031417 A1 WO2023031417 A1 WO 2023031417A1 EP 2022074489 W EP2022074489 W EP 2022074489W WO 2023031417 A1 WO2023031417 A1 WO 2023031417A1
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- group
- meth
- lubricating composition
- monomers
- polymer
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- 239000000203 mixture Substances 0.000 title claims abstract description 112
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 92
- 230000008719 thickening Effects 0.000 title claims abstract description 14
- -1 polybutylene group Polymers 0.000 claims abstract description 113
- 239000000178 monomer Substances 0.000 claims abstract description 90
- 229920000642 polymer Polymers 0.000 claims abstract description 45
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 239000002199 base oil Substances 0.000 claims abstract description 16
- 238000001879 gelation Methods 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000003599 detergent Substances 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052749 magnesium Inorganic materials 0.000 claims description 12
- 239000011777 magnesium Substances 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 11
- 239000011575 calcium Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 230000003749 cleanliness Effects 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 73
- 150000001875 compounds Chemical class 0.000 description 56
- 125000000217 alkyl group Chemical group 0.000 description 51
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- 125000004432 carbon atom Chemical group C* 0.000 description 37
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- 239000000654 additive Substances 0.000 description 29
- 150000002430 hydrocarbons Chemical class 0.000 description 24
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- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical class O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
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- 239000010949 copper Substances 0.000 description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
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- 239000003446 ligand Substances 0.000 description 3
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
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- 150000003077 polyols Chemical class 0.000 description 3
- 150000003873 salicylate salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- JDCBWJCUHSVVMN-SCSAIBSYSA-N (2r)-but-3-en-2-amine Chemical compound C[C@@H](N)C=C JDCBWJCUHSVVMN-SCSAIBSYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
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- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- GOZDOXXUTWHSKU-UHFFFAOYSA-N pentadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C=C GOZDOXXUTWHSKU-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- YCGHMIAXHZJKML-UHFFFAOYSA-N prop-1-en-2-yl dihydrogen phosphate Chemical compound CC(=C)OP(O)(O)=O YCGHMIAXHZJKML-UHFFFAOYSA-N 0.000 description 1
- XFKRSSJJDQIILX-UHFFFAOYSA-N prop-1-enyl dihydrogen phosphate Chemical compound CC=COP(O)(O)=O XFKRSSJJDQIILX-UHFFFAOYSA-N 0.000 description 1
- DZMOLBFHXFZZBF-UHFFFAOYSA-N prop-2-enyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC=C DZMOLBFHXFZZBF-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical group C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- 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
- 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
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2030/02—Pour-point; 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
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
Definitions
- the present invention relates to lubricating compositions having improved cold properties. More particularly, the present application relates to the use of a specific polymer to improve the cold thickening properties of a lubricating composition.
- the lubricating compositions comprise numerous additives and in particular detergent-type additives.
- the change in the nature of the detergents can have a significant impact on the performance of the lubricating compositions and in particular on the gel index.
- a partial change in the nature of a detergent for example calcium detergent
- a magnesium detergent generates, with an equivalent formula, a failure of the gelation index test (or Gelation Index in English) showing a thickening of the lubricating composition at very low temperature).
- API American Petroleum Institute
- An objective of the present invention is to provide additives making it possible to improve the cold thickening properties of lubricating compositions, in particular during modifications of the nature of the detergents contained in the lubricating compositions.
- Another object of the present invention is to provide a lubricating composition having good cold thickening properties.
- R 1 represents a hydrogen atom or a methyl group
- X 1 represents a group chosen from: -O-, -O(AO) m , or -NH-, each group A independently representing a C2-C4 alkylene group and m an integer ranging from 0 to 10,
- the improvement in the cold thickening properties is determined with respect to the same lubricating composition but not comprising the comb polymer.
- the cold thickening corresponds to the gelation index.
- the Gelation Index and its measurement method, are described in particular in the ASTM D1533-20a (2020) standard.
- the gel index is a measure of the apparent viscosity of engine oil at low temperatures. The resulting measurement of this test is the maximum rate of increase in viscosity.
- the (X)W-(Y) grade corresponds, in the context of the invention, to the grade of the final lubricating composition and not of the base oil alone.
- the comb polymer also comprises units derived from monomers (b) of formula (II): in which :
- R 3 represents a hydrogen atom or a methyl group
- - X 2 represents an -O- or -NH- group
- R4 groups represent, independently, a C2-C4 alkylene group
- R 5 represents a C1 -C8 alkyl group
- - q is an integer ranging from 1 to 20.
- R 1 is a methyl group.
- C2-C4 alkylene group mention may in particular be made of an ethylene group, a 1,2- or 1,3-propylene group or even a 1,2-, 1,3- or 1,4-butylene group.
- m is an integer ranging from 0 to 4, more preferably from 0 to 2.
- each A can be the same or different, and the fragments (AO) m can be linked randomly or in blocks.
- the group X 1 is a group -O- or -O(AO) m -, more preferably a group -O- or -O(CH 2 CH 2 O)-.
- R 2 is a polybutylene group.
- polybutylene group is meant within the meaning of the invention a group obtained by the elimination of a hydrogen atom from a hydrocarbon polymer containing, as essential structural unit, at least one type 1 monomer, 2 butylene or isobutylene.
- hydrocarbon-based polymer suitable for the preparation of a polybutylene group R 2 mention may in particular be made of a copolymer comprising units derived from isobutylene and/or from 1,2-butylene or even a polymer obtained by hydrogenation of the terminal double bond of a polybutadiene obtained by the 1,2 addition of buta-1,3-diene monomers.
- the hydrocarbon polymer can be a block polymer or a random polymer.
- the hydrocarbon-based polymer may also contain at least one structural unit distinct from the isobutylene or 1,2-butylene units.
- the hydrocarbon polymer may for example comprise one or more of the following units:
- this double bond can be partially or totally hydrogenated by hydrogenation.
- the isobutylene and 1,2-butylene units represent at least 30% by mole of the total number of structural units constituting the hydrocarbon polymer, preferably at least 40% by mole, preferably at least 50% by mole , preferably at least 60 mol%.
- the total number of butylene units (isobutylene and/or 1,2 butylene), relative to the total number of structural units of the hydrocarbon polymer, can be determined by analyzing the hydrocarbon polymer by 13 C nuclear magnetic resonance spectroscopy and using the following equation:
- the 13 C nuclear magnetic resonance spectrum shows a peak derived from an isobutylene methyl group at 30-32 ppm (integral value A), and a peak derived from a branched methylene group (-CH 2 -CH(CH 2 CH 3 )-) of 1,2-butylene at 26-27 ppm in integral value (integral value B).
- the total number of isobutylene and 1,2-butylene can be determined from the integral values of the peaks and an integral value (integral value C) of the peaks of all the carbon atoms of the hydrocarbon polymer.
- the monomers (a) are typically obtained by esterification or amidation of a (co)polymer (Y) containing a hydroxyl group or an amine group.
- a (co)polymer (Y) that is to say the (co)polymer containing a hydroxyl group or an amine group
- alkylene oxide (Y1) (co)polymers capable of being obtained by bringing an alkylene oxide into contact, for example ethylene oxide or propylene oxide, with a polymer chosen from: (1) a hydrocarbon polymer obtained by the polymerization of an unsaturated aliphatic hydrocarbon; (2) an unsaturated alicyclic hydrocarbon; (3) an unsaturated aromatic hydrocarbon, in particular chosen from C2-C36 olefins; and their derivatives, in the presence of an ionic polymerization catalyst, for example a sodium catalyst.
- a polymer chosen from: (1) a hydrocarbon polymer obtained by the polymerization of an unsaturated aliphatic hydrocarbon; (2) an unsaturated alicyclic hydrocarbon; (3) an unsaturated aromatic hydrocarbon, in particular chosen from C2-C36 olefins; and their derivatives, in the presence of an ionic polymerization catalyst, for example a sodium catalyst.
- the products obtained by hydroboration (Y2): (co)polymer capable of being obtained by the hydroboration of hydrocarbon polymers, in particular that described in US 4,316,973.
- Adducts of the maleic anhydride-ene-amine alcohol (Y3) type (co)polymers capable of being obtained by imidation of the product obtained by an Alder-ene reaction between a hydrocarbon polymer having a double bond and the anhydride maleic acid, in the presence of an amino alcohol.
- Products capable of being obtained by hydroformylation and hydrogenation (co)polymer(s) capable of being obtained by hydroformylation of a hydrocarbon polymer having a double bond, followed by a hydrogenation step. Mention may be made, by way of example, of the products described in JP-A 63-175096.
- Maleic anhydride-ene-ethylenediamine (Y5) adducts (co)polymers capable of being obtained by imidation of a product obtained by an Alder-ene reaction between a hydrocarbon polymer having a double bond and the anhydride maleic, in the presence of ethylenediamine.
- the (co)polymer (Y) is chosen from (co)polymers (Y1), (Y2), and (Y3), more preferably from (co)polymers (Y) and (Y1).
- the number-average molecular weight (Mn) of each of the (co)polymers (Y) is preferably from 1,000 to 25,000 g. mol -1 , more preferably from 2,000 to 20,000 g. mol -1 , particularly preferably from 3,000 to 15,000 g. mol -1 , more preferably from 4,000 to 10,000 g. mol -1 .
- the crystallization temperature of the (co)polymer (Y) is less than or equal to -40° C., more preferably less than or equal to -50° C., in particular less than or equal to -55° C., typically less than or equal to -60 °C.
- the crystallization temperature of the (co)polymer (Y) or of the (co)polymer (A) can be measured using a differential scanning calorimeter of the "Unix® DSC7" type (PerkinElmer). The crystallization temperature is measured during isothermal cooling of a sample (5 mg) of (co)polymer (Y) or (co)polymer (A) from 100°C to -80°C at a rate of 10 °C/min.
- the copolymer also comprises repeating units capable of being obtained by the polymerization of monomers (b) of formula (II): in which :
- R 3 is a hydrogen atom or a methyl group
- - X 2 is a group represented by -O- or -NH-;
- R 4 groups represent, independently, a C2-C4 alkylene group
- - q is an integer ranging from 1 to 20.
- R 3 is a methyl group.
- X 2 is an -O- group.
- C2-C4 alkylene groups mention may in particular be made of ethylene, isopropylene, 1,2- or 1,3-propylene, isobutylene and 1,2-, 1,3 - or 1,4-butylene.
- q is equal to 1 or 2.
- each R 4 can be the same or different, and the fragments (R 4 O)q can be linked randomly or in blocks.
- C1-Cs alkyl groups mention may in particular be made of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-heptyl, isoheptyl, n-hexyl, 2 -ethylhexyl, n-pentyl and n-octyl.
- C 1 -C 5 alkyl groups preference will be given to C 1 -C 6 alkyl groups, more preferably C 1 -C 5 alkyl groups, typically C 4 alkyl groups.
- monomers (b) include methoxypropyl (meth)acrylate, methoxybutyl (meth)acrylate, methoxyheptyl (meth)acrylate, methoxyhexyl (meth)acrylate, methoxybutyl (meth)acrylate, methoxypentyl, methoxyoctyl (meth)acrylate, ethoxyethyl (meth)acrylate, ethoxypropyl (meth)acrylate, ethoxybutyl (meth)acrylate, ethoxyheptyl (meth)acrylate, ethoxyhexyl (meth)acrylate , ethoxypentyl (meth)acrylate, ethoxyoctyl (meth)acrylate,
- the term “(meth)acrylate” designates a methacrylate or an acrylate.
- the term “(meth)acrylamide” designates a methacrylamide or an acrylamide.
- the monomers (b) are chosen from ethoxyethyl (meth)acrylate and butoxyethyl (meth)acrylate.
- the monomers (b) are distinct from the monomers (a).
- the copolymer of the invention may also comprise, in addition to the units derived from the monomers (a) and (b), additional repeating units capable of being obtained by the polymerization of monomers chosen from:
- monomers (c) mention may in particular be made of: methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate and butyl (meth)acrylate.
- the monomers (C) are chosen from methyl (meth)acrylate and butyl (meth)acrylate, more preferably from butyl (meth)acrylates.
- n-dodecyl (meth)acrylate n-tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, (meth) n-pentadecyl acrylate, n-hexadecyl (meth)acrylate, n-octadecyl (meth)acrylate, n-icosyl (meth)acrylate, n-tetracosyl (meth)acrylate, n-triacontyl (meth)acrylate and n-hexatriacontyl (meth)acrylate.
- the monomers (d) are chosen from alkyl (meth)acrylates having a linear C12-C28 alkyl group, more preferably from alkyl (meth)acrylates having a linear C12-C22 alkyl group.
- the (co)polymer of the invention may also contain repeating units capable of being obtained by the polymerization of monomers (e) represented by the following formula (III): in which :
- R 6 is a hydrogen atom or a methyl group
- - X 3 is an -O- or -NH- group
- R 7 groups represent, independently, a C2-C4 alkylene group
- R 8 and R 9 independently represent a linear C4-C24 alkyl group
- - r is an integer ranging from 0 to 20.
- R 6 is a methyl group.
- X 3 is an -O- group.
- C2-C4 alkylene groups mention may in particular be made of ethylene, isopropylene, 1,2- or 1,3-propylene, isobutylene and 1,2-, 1, 3- or 1,4-butylene.
- r is an integer ranging from 0 to 5, more preferably from 0 to 2.
- the R 7 groups may be identical or different, and the (R 7 O) r fragments may be linked randomly or in blocks.
- linear C4-C24 alkyl groups mention may in particular be made of n-butyl, n-heptyl, n-hexyl, n-pentyl, n-octyl, n-nonyl, n-decyl, n- undecyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl and n-tetracosyl.
- the R 8 and R 9 groups are chosen, independently, from linear C6-C24 alkyl groups, more preferably from linear C6-C20 alkyl groups, typically from linear Cs-C alkyl groups.
- monomers (e) mention may in particular be made of: 2-octyldecyl (meth)acrylate, an ester of ethylene glycol mono-2-octylpentadecyl ether and (meth)acrylic acid, ( 2-octyldodecyl meth)acrylate, 2-n-decyltetradecyl (meth)acrylate, 2-n-dodecylhexadecyl (meth)acrylate, 2-tetradecyloctadecyl (meth)acrylate, 2-dodecylpentadecyl (meth)acrylate , 2-tetradecylheptadecyl (meth)acrylate, 2-hexadecylheptadecyl (meth)acrylate, 2-heptadecylicosyl (meth)acrylate, 2-hexadecyldocosyl (meth)acrylate, 2-eicosy
- the monomers (e) are chosen from alkyl (meth)acrylates in which the alkyl group is chosen from branched C12-C36, more preferably C14-C32, typically C16-C28 alkyl groups.
- Monomers (b) to (e) are obtained by reacting a terminal hydroxyl group or an amine group of a compound comprising a hydrocarbon group with a (meth)acrylic acid, but not by modifying a hydrocarbon polymer.
- monomers (b) through (e) are not polyolefin-based monomers.
- those obtained by adding 2 to 20 moles of ethylene oxide, propylene oxide or butylene oxide to Ci-Cs alcohols and those obtained by adding 1 to 20 moles of Ethylene oxide, propylene oxide or butylene oxide to alcohols containing branched C10-C50 alkyl groups are also not obtained by modification of hydrocarbon polymers.
- these monomers are not polyolefin-based monomers.
- the (co)polymer of the invention comprises, in addition to the units derived from monomers (a) to (e), repeating units obtained by polymerization of monomers chosen from the group consisting of:
- Example of monomer (f2) 4-nitrostyrene.
- C3-C6 alkenylamines such as for example (meth)allylamine and crotylamine
- C2-C6 aminoalkyl (meth)acrylates such as, for example, aminoethyl (meth)acrylate
- monoalkylaminoalkyl (meth)acrylates in particular those comprising a C2-C6 aminoalkyl group in which a C1-C6 alkyl group is linked to a nitrogen atom, such as ( N-t-butylaminoethyl meth)acrylate and N-methylaminoethyl (meth)acrylate; C6-C12 dialkenylamines, for example di(meth)allylamine;
- dialkylaminoalkyl (meth)acrylates in particular those comprising a C2-C6 aminoalkyl group in which two C1-C6 alkyl groups are bonded to a nitrogen atom, such as ( N,N-dimethylaminoethyl meth)acrylate and N,N-diethylaminoethyl (meth)acrylate; alicyclic (meth)acrylates comprising a nitrogen atom such as, for example, morpholinoethyl (meth)acrylate; aromatic monomers such as for example N-(N',N'-diphenylaminoethyl)(meth)acrylamide, N,N-dimethylaminostyrene, 4-vinylpyridine, 2-vinylpyridine, N-vinylpyrrole, N-vinylpyrrolidone and N-vinylthiopyrrolidone], and
- the monomers (f) are chosen from monomers (f1) and (f3), more preferably from N-(N',N'-diphenylaminoethyl)(meth)acrylamide, N-(N',N' - dimethylaminoethyl)(meth)acrylamide, N-(N',N'-diethylaminoethyl)(meth)acrylamide, N-(N',N'-dimethylaminopropyl)(meth)acrylamide, (meth)acrylate of N, N-dimethylaminoethyl and N,N-diethylaminoethyl (meth)acrylate.
- - aromatic monomers containing a hydroxyl group such as p-hydroxystyrene
- C2-C6 hydroxyalkyl (meth)acrylates such as, for example, 2-hydroxyethyl (meth)acrylate and 2- or 3-hydroxypropyl (meth)acrylate
- mono- or bis-hydroxyalkyl C1 -C4 substituted (meth)acrylamides such as for example N,N-bis(hydroxymethyl)(meth)acrylamide, N,N-bis(hydroxypropyl)(meth)acrylamide and N,N-bis(2-hydroxybutyl)(meth)acrylamide
- vinyl alcohol C3-C12 alkenols, for example (meth)allylic alcohol, crotyl alcohol, isocrotyl alcohol, 1-octenol and 1-undecenol
- monools or diols of C4-C12 alkenes such as for example 1-butene-3-ol, 2-butene-1-ol and 2-but
- polyoxyalkylene glycols in which the alkylene group is C2-C4 and the degree of polymerization is from 2 to 50; polyoxyalkylene polyols such as, for example, polyoxyalkylene ethers of polyhydric alcohols comprising from 3 to 8 hydroxyl groups, the alkylene group being C2-C4, and the degree of polymerization ranging from 2 to 100; mono(meth)acrylates of C1-C4 alkyl ethers of polyoxyalkylene glycols or of polyoxyalkylene polyols such as, for example, polyethylene glycol (Mn from 100 to 300 g.mol- 1 ), polypropylene glycol mono(meth)acrylate (Mn: from 130 to 500 g.mol -1 ), methoxy polyethylene glycol mono(meth)acrylate (Mn: from 110 to 310 g.mol -1 ), the product of the addition of lauryl alcohol with oxide of ethylene (2 to 30 moles), and polyoxyethylene mono(meth)acrylate
- the monomers (h) are chosen in particular from the following monomers (h1) and (h2).
- Examples of monomers (h1) (meth)acryloyloxyalkyl C2-C4 phosphate esters such as for example (meth)acryloyloxyethyl phosphate and (meth)acryloyloxyisopropyl phosphate; alkenyl phosphate esters such as for example vinyl phosphate, allyl phosphate, propenyl phosphate, isopropenyl phosphate, butenyl phosphate, pentenyl phosphate, octenyl phosphate, phosphate decenyl and dodecenyl phosphate.
- the term "(meth)acryloyloxy” means acryloyloxy or methacryloyloxy.
- monomers (h2) (meth)acryloyloxy alkyl C2-C4 phosphonic acids such as for example (meth)acryloyloxyethyl phosphonic acid; alkenyl C2-C12 phosphonic acids such as vinylphosphonic acid, allylphosphonic acid and octenylphosphonic acid.
- the monomers (h) are chosen from monomers (h1), more preferably from (meth)acryloyloxyalkyl C2-C4 phosphate esters, advantageously the monomers (h) are (meth)acryloyloxyethyl phosphate.
- the (co)polymer of the invention comprises, in addition to the units derived from monomers (a) to (h), repeating units obtained by polymerization of monomers (i) comprising at least two unsaturated groups.
- monomer (i) mention may be made of divinylbenzene; C4-C12 alkadienes such as butadiene, isoprene, 1,4-pentadiene, 1,6-heptadiene and 1,7-octadiene; (di)cyclopentadiene; vinylcyclohexene and ethylidenebicycloheptene, limonene, ethylene di(meth)acrylate, polyalkylene oxide glycol di(meth)acrylate, pentaerythritol triallyl ether, trimethylolpropane tri(meth)acrylate, and esters disclosed in WO 01/009242 such as for example a glycolic ester of an unsaturated carboxylic acid having a number average molecular weight (Mn) greater than or equal to 500 g. mol -1 or an ester of an unsaturated alcohol and a carboxylic acid.
- Mn number average molecular weight
- the (co)polymer of the invention may also comprise, in addition to the units derived from monomers (a) to (i), repeating units obtained by polymerization of monomers chosen from:
- Examples of monomer (j) C2-C20 alkenes such as ethylene, propylene, butene, isobutylene, pentene, heptene, diisobutylene, octene, dodecene and octadecene .
- Examples of monomer (k) cyclopentene, cyclohexene, cycloheptene, cyclooctene and pinene.
- monomers (I) examples include styrene, ⁇ -methylstyrene, vinyltoluene, 2,4-dimethylstyrene, 4-ethylstyrene, 4-isopropylstyrene, 4-butylstyrene, 4- phenylstyrene, 4-cyclohexylstyrene, 4-benzylstyrene, 4-crotylbenzene, indene and 2-vinylnaphthalene.
- C1-C12 alkyl, aryl or alkoxyalkylvinyl ethers methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether; 2-
- Examples of monomers containing an epoxy group (n) glycidyl (meth)acrylate and glycidyl (meth)allyl ether.
- Examples of monomers containing a halogen (o) vinyl chloride, vinyl bromide, vinylidene chloride, (meth)allyl chloride and halogenated styrenes such as for example dichlorostyrene.
- alkyl, cycloalkyl or aralkyl esters of unsaturated polycarboxylic acids [C1-C8 alkyl diesters (dimethyl maleate, dimethyl fumarate, diethyl maleate and maleate dioctyl) of unsaturated dicarboxylic acids (such as maleic acid, fumaric acid and itaconic acid)].
- composition of the copolymer can be determined by proton nuclear magnetic resonance spectroscopy ( 1 H NMR) or by gas chromatography coupled with mass spectrometry (GC-MS).
- the monomers (a) represent from 1% to 50% by weight, relative to the total weight of the (co)polymer, more preferably from 5% to 40% by weight, in particular from 8% to 40% by weight, typically 10% to 30% by weight.
- the monomers (b) represent from 1% to 80% by weight, relative to the total weight of the (co)polymer, more preferably from 5% to 60% by weight, in particular from 10% to 35% by weight, typically 10% to 30% by weight.
- the monomers (a) and (b) together represent at least 10% by weight of the total weight of the (co)polymer, more preferably from 15% to 90% by weight, in particular from 20% to 80% by weight, typically 20% to 50% by weight.
- the monomers (c) represent from 1% to 80% by weight, relative to the total weight of the (co)polymer, more preferably from 20% to 70% by weight, in particular from 30% to 65% by weight.
- the monomers (d) represent from 1% to 40% by weight, relative to the total weight of the (co)polymer, more preferably from 1% to 35% by weight, in particular from 2% to 30% by weight.
- the monomers (e) represent from 0% to 40% by weight, relative to the total weight of the (co)polymer, more preferably from 1% to 30% by weight, in particular from 1% to 25% by weight.
- the monomers (f), (h) and (h) each represent from 0% to 15% by weight, relative to the total weight of the (co)polymer, more preferably from 1% to 12% by weight, in particular from 2% to 10% by weight.
- the monomers (i) represent from 0.01 ppm to 200 ppm by weight, relative to the total weight of the (co)polymer, more preferably from 0.005 ppm to 50 ppm by weight, in particular from 0.1 ppm to 20 ppm by weight.
- the monomers (j) to (p) each represent from 0 ppm to 10% by weight, relative to the total weight of the (co)polymer, more preferably from 1% to 7% by weight, in particular from 2% to 5% by weight.
- the copolymer has a weight average molecular weight (Mw) of 5000 g. mol -1 to 2,000,000 g. mol -1 , more preferably 150,000 g. mol -1 to 1,000,0000 g. mol -1 , in particular from 230,000 g.moM to 1,000,000 g. mol -1 , in particular 300,000 g. mol -1 at 800,000 g. mol -1 .
- Mw weight average molecular weight
- the weight average molar mass can be determined by steric exclusion chromatography with poly(methyl methacrylate) (PMMA) standards.
- the (co)polymer preferably has a crystallization temperature of less than or equal to -30°C, more preferably less than or equal to -40°C, in particular less than or equal to -50°C, typically less than or equal to -60 °C.
- copolymer implemented according to the invention can be synthesized according to any method well known to those skilled in the art or can be found commercially.
- Specific examples include a method in which the monomers are subjected to solution polymerization in a solvent in the presence of a polymerization catalyst.
- solvent examples include toluene, xylene, C9-C10 alkylbenzenes, methyl ethyl ketone and mineral oils.
- polymerization catalysts examples include azo catalysts (such as 2,2'-azobis(2-methylbutyronitrile) and 2,2'-azobis(2,4-dimethylvaleronitrile)), catalysts peroxides (such as benzoyl peroxide, cumyl peroxide and lauryl peroxide) and redox catalysts (such as mixtures of benzoyl peroxide and tertiary amines).
- azo catalysts such as 2,2'-azobis(2-methylbutyronitrile) and 2,2'-azobis(2,4-dimethylvaleronitrile)
- catalysts peroxides such as benzoyl peroxide, cumyl peroxide and lauryl peroxide
- redox catalysts such as mixtures of benzoyl peroxide and tertiary amines.
- a known chain transfer agent such as C2-C20 alkyl mercaptans
- the polymerization temperature is preferably 25°C to 140°C, more preferably 50°C to 120°C.
- the comb polymer of the invention (or (co)polymer) can also be obtained by bulk, emulsion or suspension polymerization.
- the (co)polymer when it is a copolymer, it can be one of the following types: a random addition polymer, an alternative copolymer, a graft copolymer and a block copolymer.
- the comb polymer of the invention is used in the lubricating composition, preferably in an amount ranging from 1 to 20%, preferably from 4 to 16%, by mass relative to the total mass of the lubricating composition.
- the lubricating composition according to the invention may comprise one or more friction modifiers comprising molybdenum, such that the amount of molybdenum in the lubricating composition ranges from 100 ppm to 1500 ppm by weight, preferably from 300 ppm to 1000 ppm by weight , more preferably from 500 ppm to 1000 ppm by weight, relative to the total weight of the lubricating composition.
- the quantity of molybdenum element, in particular of MoDTC compounds, of the lubricating composition according to the invention can be measured according to standard ASTM D5185.
- the lubricating composition comprises from 0.01% to 10% by weight, preferably from 0.1% to 5% by weight, more preferably from 0.5% to 3% by weight, of modifier (s) molybdenum friction, based on the total weight of the lubricating composition.
- the friction modifier(s) comprising molybdenum are chosen from organomolybdenum compounds, in particular chosen from molybdenum dithiocarbamate derivatives (MoDTC), molybdenum dithiophosphate derivatives (MoDTP) or sulfur-free molybdenum complexes, preferably still among molybdenum dithiocarbamate derivatives (MoDTC).
- Molybdenum dithiocarbamate compounds are complexes formed from a metal nucleus bonded to one or more ligands independently chosen from alkyl dithiocarbamate groups.
- the MoDTC compound of the compositions according to the invention may comprise from 1% to 40%, preferably from 2% to 30%, more preferably from 3% to 28%, even more preferably from 4% to 15% by mass of molybdenum, relative to the total mass of the MoDTC compound.
- the MoDTC compound used according to the invention can be chosen from compounds whose core comprises two molybdenum atoms (dimeric MoDTC) and compounds whose core comprises three molybdenum atoms (trimeric MoDTC).
- Trimeric MoDTC compounds generally have the formula MosSkLn in which:
- ⁇ k represents an integer at least equal to 4, preferably ranging from 4 to 10, advantageously from 4 to 7;
- ⁇ n represents an integer ranging from 1 to 4.
- ⁇ L represents an alkyl dithiocarbamate group comprising from 1 to 100 carbon atoms, preferably from 1 to 40 carbon atoms, advantageously from 3 to 20 carbon atoms.
- trimeric MoDTC compounds mention may be made of the compounds and their methods of preparation described in patent application WO-98-26030.
- the MoDTC compound used in the lubricating composition according to the invention is a dimeric MoDTC compound.
- dimeric MoDTC compounds mention may be made of the compounds and their methods of preparation described in patent application EP-0757093.
- Dimeric MoDTC compounds are generally of formula (A): in which :
- ⁇ R 1 , R 2 , R 3 and R 4 identical or different, independently represent a hydrocarbon group chosen from alkyl, alkenyl, aryl, cycloalkyl and cycloalkenyl groups; ⁇ X 1 , X 2 , X 3 and X 4 , identical or different, independently represent an oxygen atom or a sulfur atom.
- R 1 , R 2 , R 3 and R 4 which are identical or different, independently represent an alkyl group comprising from 4 to 18 carbon atoms or an alkenyl group comprising from 2 to 24 carbon atoms.
- X 1 , X 2 , X 3 and X 4 can be identical and represent a sulfur atom or else be identical and represent an oxygen atom. Also advantageously, X 1 and X 2 can represent a sulfur atom and X 3 and X 4 can represent an oxygen atom. Also advantageously, X 1 and X 2 can represent an oxygen atom and X 3 and X 4 can represent a sulfur atom.
- the MoDTC compound of formula (A) can also be chosen from at least one symmetrical MoDTC compound, at least one asymmetrical MoDTC compound and combinations thereof.
- symmetrical MoDTC compound is meant in particular a MoDTC compound of formula (A) in which the R 1 , R 2 , R 3 and R 4 groups are identical or a compound of formula (A) in which the R 1 and R 3 groups are identical and the R 2 and R 4 groups are identical.
- asymmetric MoDTC compound is meant a MoDTC compound of formula (A) in which the R 1 and R 2 groups are identical, the R 3 and R 4 groups are identical and the R 1 and R 2 groups are different from the R 3 groups. and R 4 .
- the lubricating composition according to the invention may comprise a mixture of at least one symmetrical MoDTC compound and at least one asymmetric MoDTC compound.
- R 1 and R 2 which are identical, then represent an alkyl group comprising from 5 to 15 carbon atoms and R 3 and R 4 , which are identical to and different from R 1 and R 2 , represent an alkyl group comprising from 5 to 15 carbon atoms.
- R 1 and R 2 which are identical, represent an alkyl group comprising from 6 to 10 carbon atoms and R 3 and R 4 represent an alkyl group comprising from 10 to 15 carbon atoms.
- R 1 and R 2 which are identical, can represent an alkyl group comprising from 10 to 15 carbon atoms and R 3 and R 4 can represent an alkyl group comprising from 6 to 10 carbon atoms.
- R 1 and R 2 , R 3 and R 4 which are identical, can represent an alkyl group comprising from 5 to 15 carbon atoms, preferably from 8 to 13 carbon atoms.
- the MoDTC compound is chosen from the compounds of formula (A) in which:
- ⁇ X 1 and X 2 represent an oxygen atom
- ⁇ X 3 and X 4 represent a sulfur atom
- R 1 represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms
- R 2 represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms
- ⁇ R 3 represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms
- R 4 represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms.
- the MoDTC compound can be chosen from the compounds of formula (A1)
- the MoDTC compound is a mixture:
- the ratio (S/O) of the number of sulfur atoms to the number of oxygen atoms of the MoDTC compound can generally vary from (1/3) to (3/1).
- MoDTC compounds As specific examples of MoDTC compounds, mention may be made of the Molyvan L®, Molyvan 807® or Molyvan 822® products marketed by the company R. T Vanderbilt Company or the Sakuralube 200®, Sakuralube 165®, Sakuralube 525® or Sakuralube 600® products. marketed by the company Adeka.
- the lubricating composition used according to the invention can also be implemented with an organomolybdenum compound chosen from the MoDTC compounds described in patent application WO-2012-141855.
- the MoDTP compound is chosen from the compounds of formula (B) in which R 5 , R 6 , R 7 and R 8 , which are identical or different, independently represent a hydrocarbon group chosen from alkyl, alkenyl, aryl, cycloalkyl or cycloalkenyl groups.
- MoDTP compounds As examples of MoDTP compounds, mention may be made of the Molyvan L® product marketed by the company R.T Vanderbilt Company or the Sakura-lube 300® or Sakura-lube 310G® products marketed by the company Adeka.
- the invention can also be implemented with a complex organomolybdenum compound free of sulfur and phosphorus.
- This organomolybdenum complex free of sulfur and phosphorus can be prepared using amide-type ligands, mainly prepared by reacting a source of molybdenum, for example molybdenum trioxide, and an amine derivative and acids fat comprising for example from 4 to 28 carbon atoms, preferably from 8 to 18 carbon atoms. Examples of fatty acids are derived from vegetable or animal oils.
- This organomolybdenum complex can be prepared according to the methods described in patents US-4889647, EP-0546357, US-5412130, EP-1770153. A preferred organomolybdenum complex is obtained by reaction:
- a source of molybdenum chosen from molybdenum trioxide or molybdates, preferably ammonium molybdate, in an amount sufficient to provide from 0.1 to 30%, preferably from 2 to 8.5%, in mass of molybdenum relative to the mass of complex.
- the organomolybdenum complex comprises at least one compound of formula (D) or of formula (E) or their mixture: in which :
- ⁇ L 1 and L 2 identical or different, independently represent O or NH
- ⁇ Q 1 and Q 2 identical or different, independently represent a linear or branched, saturated or unsaturated alkyl group, comprising from 3 to 30 carbon atoms, preferably from 3 to 20 carbon atoms, advantageously from 7 to 17 carbon atoms .
- This organomolybdenum complex can be prepared by reaction:
- the organomolybdenum complex comprises at least one compound of formula (D1) or of formula (D2) or their mixture: in which Q 1 independently represents a linear or branched, saturated or unsaturated alkyl group, comprising from 3 to 30 carbon atoms, preferentially from 3 to 20 carbon atoms, advantageously from 7 to 17 carbon atoms.
- the lubricating composition according to the invention may also comprise at least one calcium-based detergent and at least one magnesium-based detergent.
- the calcium-based detergent is chosen from salicylates, sulphonates, carboxylates, phenates, preferably calcium salicylate.
- the magnesium-based detergent is chosen from salicylates, sulphonates, carboxylates, phenates, preferably magnesium sulphonate.
- the lubricating composition of the invention comprises calcium-based detergent so as to have from 1200 to 2000 ppm of calcium relative to the total mass of the lubricating composition and/or comprises magnesium-based detergent so as to to have from 0 to 600 ppm of magnesium, based on the total mass of the lubricating composition.
- the lubricating composition according to the invention comprises one or more base oils.
- This base oil can be chosen from many oils.
- the base oil of the lubricating composition according to the invention may in particular be chosen from oils of mineral or synthetic origin belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) ( Table A) or mixtures thereof.
- the mineral base oils useful according to the invention include all types of bases obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, desalphatation, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofinishing. Blends of synthetic and mineral oils can also be used.
- lubricating bases there is generally no limitation as to the use of different lubricating bases to produce the lubricating compositions according to the invention, except that they must have properties, in particular of viscosity, viscosity index, sulfur content , resistance to oxidation, suitable for use in engines.
- the base oils of the lubricating compositions used according to the invention can also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, polyalkylene glycols (PAG), as well as from polyalphaolefins.
- synthetic oils such as certain esters of carboxylic acids and alcohols, polyalkylene glycols (PAG), as well as from polyalphaolefins.
- the lubricating composition according to the invention comprises at least one Group II oil and/or at least one Group III oil.
- the base oil or oils represent at least 50% by weight, preferably at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 75% by weight, of the total weight of the lubricating composition.
- the lubricating composition comprises from 50% to 99.89% by weight, preferably from 70% to 99.5% by weight, more preferably from 80% to 99% by weight of oil basestock(s), preferably including at least one Group II oil and/or at least one Group III oil and/or at least one Group IV oil and/or at least one Group V oil.
- the lubricating composition also comprises one or more other additives.
- the other preferred additives for the lubricating composition according to the invention are chosen from detergent additives, anti-wear additives, friction modifier additives with the exception of molybdenum-based friction modifiers, extreme pressure additives, dispersants other than the boron dispersants defined above, pour point improvers, viscosity index improvers, anti- foam, thickeners and mixtures thereof.
- the additives chosen from detergent additives, anti-wear additives, friction modifier additives with the exception of molybdenum-based friction modifiers, extreme pressure additives, dispersants other than boron dispersants defined above, pour point improvers, viscosity index improvers, anti-foaming agents, thickeners and mixtures thereof constitute up to 20% by weight, preferably from 0, 1% to 15% by weight, more preferably 1% to 10% by weight, of the total weight of the lubricating composition.
- the lubricating composition further comprises at least one detergent.
- Detergent additives generally reduce the formation of deposits on the surface of metal parts by dissolving secondary products of oxidation and combustion.
- the detergent additives which can be used in the lubricating composition according to the invention are generally known to those skilled in the art.
- Detergent additives can be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophilic head.
- the associated cation can be a metal cation of an alkali or alkaline earth metal.
- the detergent additives are preferably chosen from alkali metal or alkaline-earth metal salts of carboxylic acids, sulfonates, salicylates, naphthenates, as well as phenate salts.
- the alkali and alkaline-earth metals are preferably calcium, magnesium, sodium or barium. These metallic salts generally comprise the metal in a stoichiometric quantity or else in excess, therefore in a quantity greater than the stoichiometric quantity. These are then overbased detergent additives; the excess metal providing the overbased character to the detergent additive is then generally in the form of an oil-insoluble metal salt, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferentially a carbonate .
- an oil-insoluble metal salt for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferentially a carbonate .
- the lubricating composition comprising at least one detergent chosen from detergents based on calcium, detergents based on magnesium, and their mixture.
- the lubricating composition according to the invention comprises at least one calcium-based detergent and at least one magnesium-based detergent.
- the lubricating composition according to the invention may comprise from 2 to 4% by weight of detergent additive(s) relative to the total mass of the lubricating composition.
- the lubricating composition according to the invention may also additionally comprise at least one non-boronated dispersing agent.
- the non-boronated dispersing agent can be chosen from Mannich bases, succinimides and their derivatives.
- the non-boronated dispersant(s) can be chosen from non-boronated polyisobutene succinimide, and mixtures thereof.
- the lubricating composition according to the invention may comprise from 0.2% to 10% by mass of non-boronated dispersing agent, relative to the total mass of the lubricating composition.
- the lubricating composition used according to the invention may comprise at least one pour point improving additive or PPD agent (for pour point depressant or pour point reducing agent).
- PPD agent for pour point depressant or pour point reducing agent
- the pour point reducing agents generally additionally improve the cold behavior of the lubricating composition used according to the invention.
- pour point reducing agents mention may be made of polyalkyl methacrylates (different from the copolymer of the invention), polyacrylates (different from the copolymer of the invention), polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.
- the lubricating composition according to the invention may also comprise at least one anti-wear additive, at least one extreme pressure additive or mixtures thereof.
- the lubricating composition used according to the invention comprises at least one anti-wear additive.
- Anti-wear additives and extreme pressure additives protect friction surfaces by forming a protective film adsorbed on these surfaces.
- the anti-wear additives are chosen from phospho-sulphur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
- the preferred compounds are of formula Zn((SP(S)(OR a )(OR b ))2, in which R a and R b , which are identical or different, independently represent an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms
- Amine phosphates are also anti-wear additives that can be used in the lubricating composition used according to the invention.
- the phosphorus provided by these additives can act as a poison for the catalytic systems of automobiles because these additives generate ash.
- These effects can be minimized by partially replacing the amine phosphates with additives that do not provide phosphorus, such as, for example, polysulphides, in particular sulphur-containing olefins.
- the lubricating composition according to the invention may comprise from 0.01 to 6% by mass, preferentially from 0.05 to 4% by mass, more preferentially from 0.1 to 2% by mass relative to the mass total of lubricating composition, anti-wear additives and extreme pressure additives.
- the lubricating composition according to the invention may comprise at least one friction modifier additive different from the molybdenum friction modifier defined in the present invention.
- the friction modifier additive can be selected from a compound providing metallic elements and an ash-free compound.
- the compounds providing metallic elements mention may be made of complexes of transition metals such as Sb, Sn, Fe, Cu, Zn, the ligands of which may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or of phosphorus.
- the ash-free friction modifier additives are generally of organic origin and can be chosen from fatty acid and polyol monoesters, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, borate fatty epoxides; fatty amines or fatty acid glycerol esters.
- the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
- the lubricating composition according to the invention may comprise from 0.01% to 2% by mass or from 0.01% to 5% by mass, preferably from 0.1% to 1.5% by mass or from 0.1% to 2% by mass relative to the total mass of the lubricating composition, of friction modifier additive.
- the lubricating composition according to the invention may comprise at least one antioxidant additive.
- the antioxidant additive generally makes it possible to delay the degradation of the lubricating composition in service. This degradation can in particular result in the formation of deposits, in the presence of sludge or in an increase in the viscosity of the lubricating composition.
- Antioxidant additives act in particular as free radical inhibitors or hydroperoxide destroyers.
- the antioxidant additives commonly employed mention may be made of phenolic-type antioxidant additives, amine-type antioxidant additives, antioxidant additives phosphosulfur. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can be ash generators.
- the phenolic antioxidant additives may be ash-free or may be in the form of neutral or basic metal salts.
- the antioxidant additives may in particular be chosen from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C1-C12 alkyl group, N,N '-dialkyl-aryl-diamines and mixtures thereof.
- the sterically hindered phenols are chosen from compounds comprising a phenol group of which at least one carbon vicinal to the carbon bearing the alcohol function is substituted by at least one Ci-C10 alkyl group, preferably an alkyl group C1-Ce, preferably a C4 alkyl group, preferably by the ter-butyl group.
- Amino compounds are another class of antioxidant additives that can be used, possibly in combination with phenolic antioxidant additives.
- amino compounds are aromatic amines, for example aromatic amines of formula NR c R d R e in which R c represents an aliphatic group or an optionally substituted aromatic group, R d represents an optionally substituted aromatic group, R e represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R f S(O) z R 9 in which R f represents an alkylene group or an alkenylene group, R 9 represents an alkyl group, a alkenyl group or an aryl group and z represents 0, 1 or 2.
- Sulfurized alkyl phenols or their alkali metal and alkaline earth metal salts can also be used as antioxidant additives.
- antioxidant additives are that of copper compounds, for example copper thio- or dithio-phosphates, salts of copper and of carboxylic acids, dithiocarbamates, sulphonates, phenates, copper acetylaceto nates. Copper I and II salts, succinic acid or anhydride salts can also be used.
- the lubricating composition used according to the invention may contain all types of antioxidant additives known to those skilled in the art.
- the lubricating composition comprises at least one ash-free antioxidant additive.
- the lubricating composition used according to the invention comprises from 0.5 to 2% by weight relative to the total mass of the composition, of at least one antioxidant additive.
- the lubricating composition may also comprise at least one viscosity index improving polymer different from the copolymer defined herein. invention.
- polymers improving the viscosity index mention may be made of polymeric esters, homopolymers or copolymers, hydrogenated or non-hydrogenated, of styrene, butadiene and isoprene, polymethacrylates (PMA).
- the lubricating composition according to the invention may comprise from 0.1 to 15% by mass relative to the total mass of the lubricating composition of a polymer improving the viscosity index different from the copolymer defined herein. invention.
- the present invention also makes it possible to reduce pre-ignition while preferably maintaining good engine cleanliness.
- the measurement of the pre-ignition parameter is carried out by an LSPI engine test (sequence IX, ASTMD8291).
- engine is preferably meant a motor vehicle engine, in particular a 2-stroke or 4-stroke engine.
- the use according to the invention makes it possible to obtain a lubricating composition having a gelation index (or Gelation index in English) according to the ASTM D5133 standard of less than 6, in particular measured with a gradual drop in temperature to -40 °C.
- a gelation index or Gelation index in English
- R 1 represents a hydrogen atom or a methyl group
- X 1 represents a group chosen from: -O-, -O(AO) m , or -NH-, each group A independently representing a C2-C4 alkylene group and m an integer ranging from 0 to 10, R 2 is a polybutylene group, and p is equal to 0 or 1.
- the comb polymer, the lubricating composition are as defined above.
- R 1 represents a hydrogen atom or a methyl group
- X 1 represents a group chosen from: -O-, -O(AO) m , or -NH-, each group A independently representing a C2-C4 alkylene group and m an integer ranging from 0 to 10,
- R 2 is a polybutylene group, and p is equal to 0 or 1, said lubricating composition having a gelation index of less than 6.
- the comb polymer, the lubricating composition are as defined above.
- Example 1 preparation of lubricating compositions
- the lubricating compositions (CC1 comparative compositions, CL1 to CL4 compositions according to the invention), all of grade 0W-20, are prepared by mixing the compounds described in Table 2, at a temperature of the order of 60°C. The percentages indicated correspond to percentages by mass relative to the total mass of the composition. [Table 2]
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Citations (15)
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US4316973A (en) | 1979-09-10 | 1982-02-23 | The University Of Akron | Novel telechelic polymers and processes for the preparation thereof |
JPS63175096A (ja) | 1987-01-08 | 1988-07-19 | バスフ・アクチェンゲゼルシャフト | 燃料又は潤滑油組成物 |
US4889647A (en) | 1985-11-14 | 1989-12-26 | R. T. Vanderbilt Company, Inc. | Organic molybdenum complexes |
EP0546357A1 (fr) | 1991-12-09 | 1993-06-16 | R.T. VANDERBILT COMPANY, Inc. | Complèxes organiques de molybdène |
US5412130A (en) | 1994-06-08 | 1995-05-02 | R. T. Vanderbilt Company, Inc. | Method for preparation of organic molybdenum compounds |
EP0757093A1 (fr) | 1995-07-20 | 1997-02-05 | Tonen Corporation | Composition d'huile lubrifiante |
WO1998026030A1 (fr) | 1996-12-13 | 1998-06-18 | Exxon Research And Engineering Company | Compositions d'huile lubrifiante contenant des complexes de molybdene organiques |
WO2001009242A1 (fr) | 1999-07-30 | 2001-02-08 | Sanyo Chemical Industries, Ltd. | Composition de polyol polymere, son procede de production et procede de production de resine polyurethanne |
EP1770153A1 (fr) | 2005-09-23 | 2007-04-04 | R.T. Vanderbilt Company, Inc. | Procéde de préparation des composés organiques de molybdène |
WO2012141855A1 (fr) | 2011-04-15 | 2012-10-18 | R.T. Vanderbilt Company, Inc. | Compositions de dialkyldithiocarbamate de molybdène et compositions lubrifiantes les contenant |
WO2014076240A1 (fr) | 2012-11-16 | 2014-05-22 | Total Marketing Services | Composition lubrifiante |
FR3014898A1 (fr) | 2013-12-17 | 2015-06-19 | Total Marketing Services | Composition lubrifiante a base de triamines grasses |
US9683195B2 (en) * | 2014-02-25 | 2017-06-20 | Sanyo Chemical Industries, Ltd. | Viscosity index improver and lubricating oil composition |
US20180273870A1 (en) * | 2017-03-24 | 2018-09-27 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency and energy efficiency |
US20200071632A1 (en) * | 2017-03-23 | 2020-03-05 | Sanyo Chemical Industries, Ltd. | Viscosity index improver and lubricating oil composition |
-
2021
- 2021-09-03 FR FR2109231A patent/FR3126711A1/fr active Pending
-
2022
- 2022-09-02 WO PCT/EP2022/074489 patent/WO2023031417A1/fr active Application Filing
- 2022-09-02 KR KR1020247010930A patent/KR20240054340A/ko unknown
- 2022-09-02 CN CN202280059477.XA patent/CN117897469A/zh active Pending
Patent Citations (15)
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US4316973A (en) | 1979-09-10 | 1982-02-23 | The University Of Akron | Novel telechelic polymers and processes for the preparation thereof |
US4889647A (en) | 1985-11-14 | 1989-12-26 | R. T. Vanderbilt Company, Inc. | Organic molybdenum complexes |
JPS63175096A (ja) | 1987-01-08 | 1988-07-19 | バスフ・アクチェンゲゼルシャフト | 燃料又は潤滑油組成物 |
EP0546357A1 (fr) | 1991-12-09 | 1993-06-16 | R.T. VANDERBILT COMPANY, Inc. | Complèxes organiques de molybdène |
US5412130A (en) | 1994-06-08 | 1995-05-02 | R. T. Vanderbilt Company, Inc. | Method for preparation of organic molybdenum compounds |
EP0757093A1 (fr) | 1995-07-20 | 1997-02-05 | Tonen Corporation | Composition d'huile lubrifiante |
WO1998026030A1 (fr) | 1996-12-13 | 1998-06-18 | Exxon Research And Engineering Company | Compositions d'huile lubrifiante contenant des complexes de molybdene organiques |
WO2001009242A1 (fr) | 1999-07-30 | 2001-02-08 | Sanyo Chemical Industries, Ltd. | Composition de polyol polymere, son procede de production et procede de production de resine polyurethanne |
EP1770153A1 (fr) | 2005-09-23 | 2007-04-04 | R.T. Vanderbilt Company, Inc. | Procéde de préparation des composés organiques de molybdène |
WO2012141855A1 (fr) | 2011-04-15 | 2012-10-18 | R.T. Vanderbilt Company, Inc. | Compositions de dialkyldithiocarbamate de molybdène et compositions lubrifiantes les contenant |
WO2014076240A1 (fr) | 2012-11-16 | 2014-05-22 | Total Marketing Services | Composition lubrifiante |
FR3014898A1 (fr) | 2013-12-17 | 2015-06-19 | Total Marketing Services | Composition lubrifiante a base de triamines grasses |
US9683195B2 (en) * | 2014-02-25 | 2017-06-20 | Sanyo Chemical Industries, Ltd. | Viscosity index improver and lubricating oil composition |
US20200071632A1 (en) * | 2017-03-23 | 2020-03-05 | Sanyo Chemical Industries, Ltd. | Viscosity index improver and lubricating oil composition |
US20180273870A1 (en) * | 2017-03-24 | 2018-09-27 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency and energy efficiency |
Also Published As
Publication number | Publication date |
---|---|
CN117897469A (zh) | 2024-04-16 |
KR20240054340A (ko) | 2024-04-25 |
FR3126711A1 (fr) | 2023-03-10 |
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