Functionalized monomers

a functionalized monomer and monomer technology, applied in the direction of fatty acid chemical modification, detergent compounding agent, fuel, etc., can solve the problems of poor solvency, poor thermal stability, and insufficient lubricants

Inactive Publication Date: 2012-11-08
ELEVANCE RENEWABLE SCIENCES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0004]The functionalized monomers of the present invention may be difunctional or polyfunctional. These monomers offer flexibility as well as means to prepare novel derivatives with utility in a wide breadth of applications. These monomers may undergo high degrees of polymerization, resulting in polymers of unique molecular weight distributions and structural shapes, some of which may have use as specialty polymers to be employed in new applications. The term “polymer” is used herein to refer to polymers, including homopolymers and copolymers, as well as oligomers and co-oligomers.
[0005]The functionalized monomers of the present invention may be derivatized to provide compounds with unique properties that are easy to process and are bio-compatible. The functionalized monomers as well as the derivatives derived from such functionalized monomers may have utility in many applications and products, such as lubricants, functional fluids, fuels, dispersants, detergents, molded or extruded articles, pharmaceuticals, cosmetics, personal care products, adhesives, coatings, pharmaceuticals, cosmetics, personal care products, industrial cleaners, institutional cleaners, foods, beverages, oil field chemicals, agricultural chemicals, and the like. The functionalized monomers and / or derivatives may be used as base oils for lubricant's and functional fluids, and for providing functional additives for lubricants, functional fluids and fuels. When used as base oils, these functionalized monomers and / or derivatives may be referred to as functional base oils. These functional base oils may be used in the lubricants and functional fluids as base oils, and may also provide additional properties to the lubricant or functional fluid, such as dispersency, and the like, that in the past would have been provided by supplemental additives. The present invention may provide for an advantageous balance between various performance characteristics while selecting suitable monomers and derivatives that are compatible with acceptable manufacturing techniques.
[0006]The functionalized monomer may be derived from natural products, for example, natural oil, metathesized natural oil, carbohydrates, and the like. The functionalized monomer may be derived from one or more estolides. The natural oils, metathesized natural oils, carbohydrates and estolides employed herein may provide the advantage of comprising or being derived from renewable sources (e.g., vegetable oils, animal fats or oils, and the like) and may be obtained using environmentally friendly production techniques with less energy than conventional processes for making lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, including dispersants and detergents, polymeric resins, adhesives, coatings, pharmaceuticals, cosmetics, personal care products, industrial cleaners, institutional cleaners, foods, beverages, oil field chemicals, agricultural chemicals, and the like, derived from petroleum. This technology may be referred to as “green” technology.
[0007]Synthetic lubricants are commonly used in passenger car motor oils, heavy-duty diesel engine oils, marine and railroad engine lubricants, automatic transmission fluids, hydraulic fluids, gear oils, and industrial lubricants, such as metalworking fluids and lubricating greases. The purpose of these oils is to provide improved friction and wear control, rapid dissipation of heat, and the dissolution of and / or facilitating the removal of service-related contaminants. Achieving a proper balance between various performance characteristics is an important consideration in selecting a synthetic lubricant for a particular application. For example, polyolefin based lubricants typically exhibit good low-temperature properties, high viscosity index, and excellent thermal stability, but poor solvency. As a result, these lubricants tend to be inadequate without the presence of additional polar base stock-containing components. Conversely, polar base stock-containing lubricants, such as those based on synthetic esters and vegetable oils, typically exhibit good solvency and high surface affinity. However, these lubricants tend to be inadequate with respect to resistance to wear. The problem, therefore, is to provide a synthetic lubricant that exhibits both good solvency and good resistance to wear reduction characteristics. This invention provides a solution to this problem.
[0009]Detergents (e.g., metal-containing detergents that form ash upon combustion) are used as additives in lubricants and functional fluids to prevent oxidation-derived deposits from separating on surfaces and impairing function. Lubricants and functional fluids that typically employ these additives include passenger car motor oils, heavy-duty diesel engine oils, marine and railroad engine lubricants, and to a lesser degree automatic transmission fluids, gear oils, and the like, with the largest use typically being in automotive and industrial engine oils. The amount of detergent used in a lubricant or functional fluid depends upon the specific application but, typically, constitutes from about 0.1 percent to about 35 percent by weight of the lubricant or functional fluid. The problem is to provide detergents having improved tendencies for neutralizing acidic combustion and fuel oxidation-derived deposit precursors, and for suspending these by-products and their resultant salts in oil, thereby controlling corrosion and reducing the formation of surface deposits. This invention provides a solution to this problem.

Problems solved by technology

For example, polyolefin based lubricants typically exhibit good low-temperature properties, high viscosity index, and excellent thermal stability, but poor solvency.
As a result, these lubricants tend to be inadequate without the presence of additional polar base stock-containing components.
However, these lubricants tend to be inadequate with respect to resistance to wear.
The problem, therefore, is to provide a synthetic lubricant that exhibits both good solvency and good resistance to wear reduction characteristics.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0374]The following example discloses the oligomerization of 1-decene with methyl 9-decenoate (which may be referred to as 9-DAME or 9-DAMe) in the presence of di-t-amyl peroxide. The reaction proceeds according to the following equation using the reagents shown in the table below.

1-decene9-DAMEdi-t-amyl peroxideFW140.27184.28174.28equivalents10.001.00*mol0.80460.08050.1408**g112.8614.8324.54d (g / ml)0.740.900.82ml152.316.530.00*Note:9-DAME is 9.09 mol % of the total monomer mixture.**1.75X “the original” peroxide loading

The following process steps are followed:

[0375]A 250 ml 3-necked round-bottomed flask, equipped with a magnetic stirrer, inert gas inlet / outlet, rubber septum, thermocouple controlled heating mantle, and Dean-Stark trap with condenser, is charged with 1-decene and 9-DAME. The monomer mixture is sparged with inert gas for 1 hour to overnight.

[0376]After sparging, the monomer mixture is heated to 150° C. After reaching reaction temperature, the first 1 / 10 volume portio...

example 2

[0398]The following example discloses a process for the maleinization of methyl 9-decenoate (9-DAME). 9-DAME is reacted with maleic anhydride in an ene reaction to introduce one to two succinic groups per ester. Maleic anhydride is known to participate in ene reactions; this is due to the combined electron-withdrawing power of the two carbonyl groups adjacent to the double bond. The mechanism is believed to involve an allylic shift of one double bond by transferring the allylic hydrogen to the enophile and generating a new bond. The reaction may be promoted by heat and / or Lewis acids. In this reaction no catalyst is used.

[0399]2532.9 g (13.74 mol) 9-DAME and 1684.8 g (17.18 mol, 1.25 eq) of maleic anhydride are added into a 5 L three neck flask equipped with a large egg-shaped magnetic stirbar. The flask is then set into a heating mantel (two piece soft heating mantel with zipper). Two condensers are attached, one for incoming nitrogen gas and the other one for the outgoing gas flow...

example 3

[0400]The following example discloses a process for the maleinization of 9-octadecenoic acid dimethyl ester (ODDA FAME). After filtration over silica gel 1277.7 g (3.75 mol) of ODDA FAME are reacted with 441.5 g (4.50 mol, 1.2 eq) of maleic anhydride. After a reaction time of 6 hours at 200° C. the product is stripped in high vacuum to remove unreacted maleic anhydride. The product is a viscos, brown oil, which is transparent in smaller volumes. NMR shows no residual free maleic anhydride in the stripped product. The AV for the product is 233.8. The conversion is 91.4%. The KV (cSt) at 100° C. is 17.32. The product may be represented by the following formula:

Oxidized Derivative

[0401]The functionalized monomer or functionalized polymer of the invention may be reacted with one or more oxidizing agents. This may result in the formation of one or more oxidized derivatives which may be in the form of one or more epoxides. These may be referred to as polyfunctionalized monomers or polymer...

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Abstract

This invention relates to functionalized monomers which are reacted with an enophilic reagent (e.g., maleic anhydride) to form an enophilic reagent modified functionalized monomer. The enophilic reagent modified functionalized monomer may be further reacted with one or more additional reagents (e.g., oxygen-containing reagents, nitrogen-containing reagents, metals or metal compounds). The invention relates to base oils which may comprise functional base oils. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and functional compositions (e.g., cleaning solutions, food products, etc.).

Description

[0001]This application is a continuation-in-part under 35 U.S.C. §120 of U.S. application Ser. No. 13 / 281,108, filed Oct. 25, 2011. A claim of priority for this application under 35 U.S.C. §119(e) is hereby made to the following U.S. provisional patent applications: U.S. Ser. No. 61 / 510,159 filed Jul. 21, 2011; U.S. Ser. No. 61 / 467,273 filed Mar. 24, 2011; U.S. Ser. No. 61 / 467,275 filed Mar. 24, 2011; U.S. Ser. No. 61 / 467,276 filed Mar. 24, 2011; U.S. Ser. No. 61 / 467,279 filed Mar. 24, 2011; and U.S. Ser. No. 61 / 467,292 filed Mar. 24, 2011. These applications are incorporated herein by reference.TECHNICAL FIELD[0002]This invention relates to functionalized monomers, and to lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, dispersants, detergents, polymeric resins or plastics, adhesives, coatings, pharmaceuticals, cosmetics, personal care products, industrial cleaners, institutional cleaners, foods, beverages, oil field chemi...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C10M125/10C10L1/188C10L1/19C10M133/40C10M133/48C07C57/12C10M133/44C10M129/70C07C69/533C07C57/03C07C69/58C10L1/224C10M133/46
CPCC08F20/68C10N2260/06C10N2230/08C10M2219/046C10M2201/062C10M107/32C10N2220/022C10M149/02C10M2215/08C10M133/16C08F210/14C10N2270/02C10M2209/1023C10M145/08C10M2207/123C10N2210/02C10N2210/05C10N2220/021C10N2240/10C10N2210/04C10N2260/09C11C3/00C11D3/3746C10M2205/0285C10M2219/044C10N2210/01C08F122/105C10M2203/1025C10M2205/028C11C3/003C10N2210/03C10L1/1883C10M2209/04C10M129/72C10L1/1905C10M159/20C10M2217/06C10M2207/282C08F120/10C10M2203/1006C10N2250/10C08F20/14C10M2215/28C10M2201/02C10L1/224C08F120/04C08F2220/1866C08F220/64C08F220/10C08F220/04C08F2222/104C07D307/60C08F122/1006C10N2010/06C10N2010/10C10N2010/08C10N2010/02C10N2020/04C10N2010/04C10N2020/02C10N2030/08C10N2040/25C10N2050/10C10N2060/06C10N2060/09C10N2070/02C08F220/1809C08F222/104C10M129/68C10N2030/06C10N2030/70C10M135/04C10M135/06C10M2219/022C10M2219/024
Inventor DIBIASE, STEPHEN A.RIZVI, SYED Q.A.HATEGAN, GEORGETA
Owner ELEVANCE RENEWABLE SCIENCES INC
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