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CA-2995956-C - AZOLE DERIVATIVES AS LUBRICATING ADDITIVES

CA2995956CCA 2995956 CCA2995956 CCA 2995956CCA-2995956-C

Abstract

Lubricating compositions comprising an azole-acrylic adduct formed by contacting an azole compound with an acrylic. The adduct formed has at least one nitrogen-alkyl group comprising at least one acyl. The lubricating composition also comprises an antiwear agent and an antioxidant. Methods of lubricating an internal combustion engine comprising contacting the internal combustion engine with the lubricating composition comprising an azole-acrylic adduct formed by contacting an azole compound with an acrylic. Methods of reducing corrosion and/or seal deterioration in an internal combustion engine. The use of an azole-acrylic adduct in a lubricating composition to reduce corrosion and/or seal deterioration in an internal combustion engine.

Inventors

  • Yanshi Zhang
  • Nga H. Nguyen

Assignees

  • THE LUBRIZOL CORPORATION

Dates

Publication Date
20260505
Application Date
20160817
Priority Date
20150820

Claims (16)

  1. 31 CLAIMS 1. A lubricating composition comprising: an oil of a lubricating viscosity; 0.1 to 0.5 wt% of an azole-acrylic adduct represented by formula (II) or (III): (II) or (III) wherein R2 and R3 , are independently a hydrogen or a C1-C20 hydrocarbyl group or, when taken together, R2 and R3 form a saturated or unsaturated ring containing 5 to 6 carbon atoms; wherein R4 is a C2-C40 hydrocarbyl group comprising at least one acyl, wherein the hydrocarbyl group is linear, branched, homocyclic, or heterocyclic, or a combination thereof; wherein X1 is N or C; and wherein X2 and X3 are independently N or C-R5 , wherein R5 is a hydrogen or a C1-C12 hydrocarbyl group, and wherein at least one of X1 , X2 , and X3 are N; an antiwear agent containing phosphorus and present in an amount such that the lubricating composition has at least 300 ppm phosphorus based on a total weight of the lubricating composition; and an antioxidant.
  2. 2. The lubricating composition of claim 1, wherein the azole-acrylic adduct is a reaction product of one or more acrylic compounds with one or more azole compounds, wherein the one or more acrylic compounds comprise one or a combination of (meth)acrylate, (meth)acrylic acid, and (meth)acrylamide.
  3. 3. The lubricating composition of claim 2, wherein the one or more acrylic compounds comprise a (meth)acrylate having the formula (I): 32 (I) wherein R is a hydrogen or a methyl group and R1 is a C1-C20 hydrocarbyl group.
  4. 4. The lubricating composition of claim 3, wherein the (meth)acrylate comprises one or a combination of acrylate and methacrylate.
  5. 5. The lubricating composition of claim 1, wherein the azole-acrylic adduct is a reaction product of one or more acrylic compounds with one or more azole compounds, wherein the one or more acrylic compounds comprise one or a combination of methacrylate, methacrylic acid and methacrylamide.
  6. 6. The lubricating composition of claim 1, wherein the azole-acrylic adduct is a reaction product of one or more acrylic compounds with one or more azole compounds, wherein the one or more acrylic compounds comprise one or a combination of octadecyl acrylate, hexadecyl acrylate, tridecyl acrylate, dodecyl acrylate, decyl acrylate, 2-propylheptyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, hexyl acrylate, butyl acrylate, ethyl acrylate and methyl acrylate.
  7. 7. The lubricating composition of claim 1, wherein the azole-acrylic adduct is a reaction product of one or more acrylic compounds with one or more azole compounds, wherein the one or more acrylic compounds comprise one or a combination of octadecyl methacrylate, hexadecyl methacrylate, tridecyl methacrylate, dodecyl methacrylate, decyl methacrylate, 2-propylheptyl methacrylate, 2-ethylhexyl methacrylate, octyl acrylate, hexyl methacrylate, butyl methacrylate, ethyl methacrylate and methyl methacrylate.
  8. 8. The lubricating composition of claim 1, wherein the azole-acrylic adduct has the formula (IV): 33 (IV) wherein R6 is hydrogen or a C1-C20 hydrocarbyl group; R 7 is attached to a nitrogen atom and is a linear C2 hydrocarbyl group; and R 8 is a C1-C20 hydrocarbyl group and is linear, branched, homocyclic, heterocyclic, or a combination thereof.
  9. 9. The lubricating composition of claim 1, wherein the azole-acrylic adduct comprises at least one adduct having the formula (V), (VI), (VII), (VIII), (IX), or (X): (V) (VI) (VII) 34 (VIII) (IX) N N N O O R 6 (X) wherein R6 is hydrogen or a C1-C20 hydrocarbyl group.
  10. 10. The lubricating composition of any one of claims 1 to 9, further comprising at least one nitrogen-containing dispersant.
  11. 11. The lubricating composition of any one of claims 1 to 10, further comprising at least one boron-containing compound.
  12. 12. The lubricating composition of claim 11, wherein the boron-containing compound comprises at least one borate ester, borate alcohol, or combinations thereof.
  13. 13. The lubricating composition of any one of claims 1 to 12, further comprising at least one overbased detergent.
  14. 14. A method of lubricating an internal combustion engine comprising contacting the internal combustion engine with the lubricating composition of any one of claims 1 to 13.
  15. 15. Use of the lubricating composition as defined in any one of claims 1 to 13 to reduce corrosion and/or seal deterioration in an internal combustion engine.
  16. 16. A method of reducing corrosion and/or seal deterioration in an internal combustion engine comprising contacting the internal combustion engine with the lubricating composition of any one of claims 1 to 13.

Description

WO 2017/031143 PCT /0S2016/04 7243 AZOLE DERIVATIVES AS LUBRICATING ADDITIVES FIELD OF THE INVENTION [0001] The field of the disclosed technology is generally related to lubricating 5 compositions comprising azole derivatives. BACKGROUND OF THE INVENTION [0002] It is well known for lubricating oils to contain a number of surface active additives (including antiwear agents, dispersants, or detergents) used to protect internal combustion engines from wear, soot deposits and acid build up. Often, such surface 10 active additives including zinc dialkyldithiophosphates (ZDDP) or dispersants can have harmful effects on bearing corrosion, dispersancy or friction performance. These additive chemistries may be corrosive to lead or copper present in bearings and other metal engine components derived from alloys using copper or lead. [0003] It is difficult for formulators to meet the present engine oil specifications by 15 employing certain beneficial additives while also meeting the specification for lead or copper corrosion. Commonly used copper corrosion inhibitors include azoles or their derivatives, such as methyl benzyl triazole (often referred to as tolyltriazole or simply, "TTZL"). Both TTZL and TTZL derivatives may have disadvantages in certain applications. TTZL is a solid that melts at 80 °C, making it difficult to blend or suspend 20 in the lubricating oil manufacturing process. TTZL may also contribute to lead corrosion under some circumstances. Some TTZL derivatives may contribute to seal wear in certain applications. Thus, TTZL and its known derivatives have not sufficiently addressed the corrosion inhibition needs in lubricating oils. SUMMARY OF THE INVENTION 25 [0004] It was surprisingly determined, however, that azole derivatives made with acrylics inhibit copper corrosion with minimal detriment to lead corrosion and seal wear. These derivatives are oil-soluble liquids at room temperature, making them easier to blend or suspend in lubricating oils than their TTZL or TTZL derivative precursors. Accordingly, in one embodiment, lubricating compositions comprising an 30 azole-acrylic adduct formed by contacting an azole compound with an acrylic is disclosed. The adduct formed has at least one nitrogen-alkyl (or "N-alkyl") group WO 2017/031143 PCT /0S2016/04 7243 comprising at least one acyl. The lubricating composition also comprises an antiwear agent and an antioxidant. [0005] The acrylic may comprise at least one (meth)acrylate, (meth)acrylic acid, (meth)acrylamide, or combinations thereof. As used herein, the term "acrylic" includes 5 derivatives of acrylic or methacrylic acids, salts, or amides. Further, the term "(meth)acrylate" and related terms includes both acrylate and methacrylate groups, ie. the methyl group is optional. Accordingly, in some embodiments, the acrylic may comprise at least one acrylate, acrylic acid, acrylamide, methacrylate, methacrylic acid, methacrylamide, or combinations thereof. In one embodiment, the acrylic may be a 10 (meth)acrylate having the formula (I): O-R1 (I) wherein Risa hydrogen or a C1-C20 hydrocarbyl group and R1 is a C1-C20 hydrocarbyl group. In another embodiment, R may be a hydrogen or a methyl group. 15 [0006] In one embodiment, the (meth)acrylate may comprise at least one acrylate, methacrylate, or combinations thereof. Suitable acrylates include, but are not limited to, octadecyl acrylate, hexadecyl acrylate, tridecyl acrylate, dodecyl acrylate, decyl acrylate, 2-propylheptyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, hexyl acrylate, butyl acrylate, ethyl acrylate, methyl acrylate, or combinations thereof. Suitable 20 methacrylates include, but are not limited to, octadecyl methacrylate, hexadecyl methacrylate, tridecyl methacrylate, dodecyl methacrylate, decyl methacrylate, 2- propylheptyl methacrylate, 2-ethylhexyl methacrylate, octyl acrylate, hexyl methacrylate, butyl methacrylate, ethyl methacrylate, methyl methacrylate, or combinations thereof. 25 [0007] In yet another embodiment, the acrylic may comprise at least one of octadecyl acrylate, hexadecyl acrylate, tridecyl acrylate, dodecyl acrylate, decyl acrylate, 2- propylheptyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, hexyl acrylate, butyl acrylate, ethyl acrylate, methyl acrylate, or combinations thereof. WO 2017/031143 PCT /0S2016/04 7243 [0008] Suitable azole compounds for making the azole-acrylic adducts include, but are not limited to, benzotriazole, benzotriazole derivatives, imidazole, imidazole derivatives, 1,2,3-triazole, 1,2,3-triazole derivatives, 1,2,4-triazole, 1,2,4-triazole derivatives, 1,3,4-triazole, 1,3,4-triazole derivatives, benzimidazole, benzimidazole 5 derivatives, pyrazole, pyrazole derivatives, 1,4-methyl benzotriazole, or combinations thereof. [0009] In one embodiment, the lubricating composition may comprise an azoleacrylic adduct represented by formula (II) or (III): (II) or (III) 10 wherein R 2 and R3 are independently a hydrogen or C1-C20 hydrocarbyl group