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
  • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
  • C10M159/12—Reaction products
  • C10M159/16—Reaction products obtained by Mannich reactions
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
  • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
• • 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
  • C10N2030/04—Detergent property or dispersant property

Definitions

• the present application is directed to a novel process for making detergents and fuel compositions comprising the detergents.
• DIG Direct injection gasoline
• Mannich base fuel additives are well known in the petroleum industry for controlling such deposit problems. However, while Mannich base additives traditionally provide excellent control for intake valve deposits, they may not control deposits to a desired degree for injectors in PFI and/or DIG engines. There is, therefore, a desire in the petroleum industry to produce fuel additives suitable for use in PFI and/or DIG engines that can provide improved control of engine deposits, and to develop methods for producing such fuel additives.
• an embodiment of the present application is directed to a process for forming a detergent base product.
• the process comprises forming a bis-Mannich intermediate compound by reacting (i) at least one hydroxyl substituted aromatic ring compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; (ii) at least one primary amine; and (iii) at least one aldehyde.
• the resulting bis-Mannich intermediate compound is then reacted with at least one second amine compound chosen from primary and secondary amines to form the detergent base product.
• Another embodiment of the present application is directed to a process for forming a Mannich reaction product,
• the process comprises reacting at least one amine compound chosen from primary and secondary amines with a bis-Mannich compound having a formula III,
• R 1 is chosen from a hydrogen radical and C 1-6 alkyl
• R 3 is a hydroxyaromatic compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000
• R 4 is a linear, branched, or cyclic, substituted or unsubstituted, saturated or unsaturated alkyl amine group.
• Another embodiment of the present application is directed to a fuel composition
• a fuel composition comprising: a base fuel; and a detergent base product comprising a mixture of formulae (VI) and (Vl),
• R 1 and R 3 are substituents independently chosen from a hydrogen radical, C 1-6 alkyls and hydrocarbyl substituents having a number average molecular weight in the range of about 500 to about 3000, with the proviso that at least one of R 1 and R 3 is a hydrocarbyl substitutent;
• R 4 is a substituent chosen from alkyl, aryl, alkenyl, alkyl amino, dialkyl amino, alkylaminoalkyl, and dialkylaminoalkyl groups;
• R 5 and R 6 are each independently chosen from a hydrogen radical, alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups, with the proviso that at least one of R 5 and R 6 is not a hydrogen radical.
• the process of the present application involves formation of a detergent base product using a bis-Mannich intermediate.
• the reaction mechanism can include a two stage process, wherein the bis-Mannich intermediate is formed during the first stage, and then reacted with an amine during the second stage to form the detergent base product. The reactions of the first and second stage will now be described.
• the bis-Mannich intermediate compounds can be formed by reacting (i) at least one hydroxyl substituted aromatic ring compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; (ii) at least one primary amine; and (iii) at least one aldehyde. Any hydroxyl substituted aromatic ring compound readily reactive in the Mannich condensation reaction may be employed.
• Representative hydroxyl substituted aromatic ring compounds used in forming the bis-Mannich intermediates of the present application are represented by the following formula I:
• R 1 , R 2 and R 3 can each be independently chosen from a hydrogen radical, a C 1-6 alkyl, or a hydrocarbyl substitutent having a number average molecular weight in the range of about 500 to about 3000, with the proviso that at least one of R 1 , R 2 and R3 is a hydrocarbyl substitutent.
• Representative C 1-6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl.
• hydrocarbyl substituents can include polypropylene groups; polybutene groups, polyisobutylene groups; polyalpha-olefin groups, such as poly 1-octene groups; and ethylene/alpha-olefin copolymer groups. Other similar long-chain hydrocarbyl substituents may also be used.
• Examples include copolymer groups having at least one monomer chosen from butylene, isobutylene, and propylene, and at least one monomer chosen from mono-olefinic comonomers copolymerizable therewith, such as ethylene, 1-pentene, 1-hexene, 1-octene, 1-decene, etc., where the copolymer molecule contains at least 50% by weight, of butylene and/or isobutylene and/or propylene units.
• the comonomers polymerized with propylene or such butenes may be aliphatic and can also contain non-aliphatic groups, e.g., styrene, o-methylstyrene, p-methylstyrene, divinyl benzene and the like.
• the resulting polymers and copolymers used in forming the compound of formula (I) are substantially aliphatic hydrocarbon polymers.
• the hydrocarbyl substituents may be substantially saturated, containing only residual unsaturation.
• the hydrocarbyl substituent is a polybutylene group.
• polybutylene is used in a generic sense to include polymers made from “pure” or “substantially pure” 1 -butene or isobutene, and polymers made from mixtures of two or all three of 1-butene, 2-butene and isobutene. Commercial grades of such polymers may also contain insignificant amounts of other olefins.
• high reactivity polyisobutenes having relatively high proportions of polymer molecules with a terminal vinylidene group can be used to form the hydrocarbyl substituent.
• at least 20% of the total terminal oletinic double bonds in such high reactivity polyisobutenes can comprise an alkylvinylidene isomer.
• at least 50%, and in other examples, at least 70%, of the total terminal olefinic double bonds can comprise an alkylvinylidene isomer.
• Suitable high reactivity polyisobutenes are disclosed, for example, in U.S. Pat. No. 4,152,499 and W.
• German Offenlegungsschrift 29 04 3144 the disclosures of which are herein incorporated by reference in their entirety.
• ethylene alpha-oletin copolymers having a number average molecular weight of 500 to 3000, wherein at least about 30% of the polymer's chains contain terminal ethylidene unsaturation can be used to form the hydrocarbyl substituent.
• the compound of formula (I) can be obtained by alkylating o-cresol with the high molecular weight hydrocarbyl polymers described above.
• an o-cresol such as ortho methyl phenol
• PIB polyisobutylene
• Suitable methods of alkylating the hydroxyaromatic compounds of the present disclosure are well known in the art. Examples of some suitable well known methods for forming hydroxyl substituted aromatic ring compounds are taught in GB 1,159,368 and U.S. Pat. Nos. 4,238,628; 5,300,701, 5,876,468, and 6,800,103, the disclosures of all of which are herein incorporated by reference in their entirety.
• R 1 of the hydroxyl substituted aromatic ring compound of formula I can be a C 1-4 alkyl
• R 2 can be a hydrogen radical
• R 3 can be a hydrocarbyl substituent chosen from the hydrocarbyl substituents described above.
• R 1 can be methyl
• R 2 can be a hydrogen radical
• R 3 can be a polyisobutylene group.
• both R 1 and R 2 are hydrogen radicals
• R 3 is a hydrocarbyl substituent chosen from the hydrocarbyl substituents described above.
• Amines which may be employed in the first stage of the reaction include any primary amines suitable for use in Mannich reactions for forming the bis-Mannich intermediate.
• the primary amine can have the formula (II):
• R 4 can be any substituent chosen from alkyl, aryl, alkenyl, alkyl amine, dialkyl amine, alkylaminoalkyl, and dialkylaminoalkyl groups.
• suitable secondary amines include dimethylamine, diethylamine, dipropylamine, dibutylamine, and dipentylamine.
• suitable primary amines include cyclohexaneamine; 1,3-propanediamine; 1,2-ethane diamine; 1,4-butanediamine; 1,6-hexanediamine; 1,2-cyclohexanediamine; 1,2-diamino-3-methyl cyclohexane; 1,2-diamino-4-methyl cyclohexane; N-aminomethyl-11-methanediamine and 3,3-dimethyl amino propyl amine.
• the amine of formula (II) may be a hydrocarbon chain substituted at one end with a primary amino group, and substituted at the other end with a primary, secondary, or tertiary amino group.
• R 4 of the compound of formula (II) can be —C 1-8 NNR′R′′, where the C 1-8 portion of the substituent is a straight or branched chain alkyl, and R′ and R′′ can be independently chosen from H, methyl, ethyl, propyl and butyl substituents.
• Examples of such compounds include dialkylaminoalkyl amines, such as dimethylaminopropyl amine, diethylaminopropyl amine, and dimethylaminobutyl amine.
• aldehydes suitable for use in a Mannich reaction can be employed in the preparation of the bis-Mannich intermediate.
• suitable aldehydes include aliphatic aldehydes; such as formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, and stearaldehyde.
• Aromatic aldehydes which may be used include benzaldehyde and salicylaldehyde.
• Illustrative heterocyclic aldehydes for use herein are furfural and thiophene aldehyde, etc.
• formaldehyde-producing reagents such as paraformaldehyde.
• the chosen aldehyde is formaldehyde.
• the reactants can be mixed in a ratio of about: 1 mole of hydroxyl substituted aromatic ring compound; about 0.3 to about 0.7 moles of primary amine; and from about 0.8 to about 1.5 moles aldehyde.
• the reactants can be mixed in a ratio of about: 1 mole of hydroxyl substituted aromatic ring compound; about 0.5 moles of primary amine; and about 1 mole aldehyde.
• the condensation reaction among the hydroxyl substituted aromatic ring compounds, the primary amines and the aldehydes is conducted at a temperature in the range of about 40° C. to about 200° C.
• the reaction can be conducted with or without a diluent or solvent.
• suitable solvents include aromatic solvents, such as xylenes, toluene, mesitylene, Aromatic 100, and heptane, or mixtures of such solvents.
• Water is evolved during the reaction and can be removed by azeotropic distillation during the course of the reaction. Typical reaction times range from 2 to 4 hours, although longer or shorter times can be used as necessary.
• the resulting bis-Mannich intermediate compound is a compound of formula (Ill):
• the bis-Mannich intermediate includes two hydroxyl substituted aromatic ring groups formed from the reactant compounds of formula (I) above, which are bridged together with a tertiary amine group.
• the bis-Mannich intermediate can be used to form the desired detergent base products in a second stage reaction, which will be described below.
• the bis-Mannich intermediate of formula (III) can be reacted with a primary or secondary amine to form a desired detergent base product.
• the primary or secondary amine can be an amine of formula (IV):
• R 5 and R 6 are each independently chosen from a hydrogen radical, alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups, with the proviso that at least one of R 5 and R 6 is not a hydrogen radical.
• the alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups can be unsubstituted, or substituted with suitable functional groups, such as carbonyl groups, hydroxyl groups and amino groups.
• the alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups can have, for example, from 1 to 30 carbon atoms, such as from 1 to 18 carbon atoms, or in other examples, from 1 to 6 carbon atoms.
• R 6 is chosen to be a hydrogen radical, and R 5 is an alkyl group substituted with a primary amine.
• the resulting amine is a diamine of formula (V):
• R 7 is a linear, branched, or cyclic alkyl group having from 1 to 10 carbon atoms.
• R 7 can be a saturated, straight chain hydrocarbon having 1 to 6 carbon atoms.
• R 7 can be a substituted or unsubstituted cycloalkane having a 4 to 8 carbon member ring, which can optionally be substituted with one or more methyl, ethyl or propyl groups.
• suitable secondary amines include dimethylamine, diethylamine, dipropylamine, dibutylamine, and dipentylamine.
• suitable primary amines include cyclohexaneamine; 1,3-propanediamine; 1,2-ethane diamine; 1,4-butanediamine; 1,6-hexanediamine; 1,2-diaminocyclohexane (DACH); 1,2-diamino-3-methyl cyclohexane; 1,2-diamino-4-methyl cyclohexane; N-aminomethyl-1,1-methanediamine and 3,3-dimethyl amino propyl amine.
• DACH 1,2-diaminocyclohexane
• DACH 1,2-diamino-3-methyl cyclohexane
• 1,2-diamino-4-methyl cyclohexane N-aminomethyl-1,1-methanediamine and 3,3-dimethyl amino propyl amine.
• the bis-Mannich intermediate of formula (III) is mixed and reacted with the primary or secondary amines of formula (IV). Any suitable proportions of the reactants that will result in formation of the desired final products can be used. In one embodiment, the reactants can be mixed in a ratio of about 1 mole of primary or secondary amine for each mole of bis-Mannich intermediate.
• the reaction can be conducted in the range of about 125° C. to about 200° C., such as about 150° C. Reaction times can range from 2 to 4 hours, although longer or shorter times can be used as necessary. Solvents from the first state of the reaction can be present during the second stage of the reaction, and/or additional suitable solvents may be added during the second stage, if desired.
• R 1 , R 3 , R 4 , R 5 and R 6 are defined as set forth above.
• the reaction cleaves the bis-Mannich intermediate of Formula (III) to form two hydroxyl substituted aromatic ring compounds that are each substituted with an amine group, in addition to the R 1 , R 3 and hydroxyl substituents.
• Formula (VI) is substituted with an amine group formed from the primary amine reactant of the first stage of the reaction, while formula (VIl) is substituted with an amine group formed from the primary or secondary amine reactant of the second stage of the reaction.
• the products of the reaction include an amine substituted compound of formula (VI) as described above.
• the product also comprises a primary amine substituent on one of the hydroxyl substituted aromatic ring compounds, as shown below in formula (VIII):
• the ratio of the compound of formula VI to the compound of formula VIII in the product mixture may vary depending on such things as reaction conditions and/or the reactants employed.
• the ratio of the compound of formula VI to the compound of formula VIII may range from about 1:4 to about 4:1. In some embodiments, the ratio may be about 1:1.
• the amine substituted products of the present application can be used as a detergent base in fuel compositions.
• the detergent base can be used in fuel additive concentrates, which can be packaged and sold to consumers separately from the base fuel.
• the additive concentrates of this invention can contain, for example, from about 12 to about 69 wt %, and for example from about 22 to about 50 wt % of the detergent on an active ingredient basis.
• the additive concentrates may also contain carrier fluid, the level of which is determined by the desired carrier to detergent base ratio.
• the carrier fluid can be of various types, such as for example liquid poly- ⁇ -olefin oligomers, liquid polyalkene hydrocarbons (e.g., polypropene, polybutene, polyisobutene, or the like), liquid hydrotreated polyalkene hydrocarbons (e.g., hydrotreated polypropene, hydrotreated polybutene, hydrotreated polyisobutene, or the like), mineral oils, hydrotreated mineral oils, liquid poly(oxyalkylene) compounds, liquid alcohols or polyols, liquid esters, and similar liquid carriers or solvents. Mixtures of two or more such carriers or solvents can be employed.
• liquid poly- ⁇ -olefin oligomers liquid polyalkene hydrocarbons (e.g., polypropene, polybutene, polyisobutene, or the like)
• liquid hydrotreated polyalkene hydrocarbons e.g., hydrotreated polypropene, hydrotreated polybutene, hydrotreated polyisobutene, or the like
• the detergent base and carrier fluid are employed in amounts sufficient to reduce or inhibit deposit formation in an internal combustion engine.
• the fuels can contain minor amounts of the detergent base and of the liquid carrier fluid proportioned as above that control or reduce formation of engine deposits, such as intake valve and injector deposits.
• the fuels of this disclosure can contain on an active ingredient basis, an amount of the Mannich base detergent in a range of about 5 to about 300 ptb (pounds by weight of additive per thousand barrels by volume of fuel), such as, for example, in the range of about 10 to about 200 ptb.
• the active ingredient basis excludes the weight of (i) unreacted components such as polyalkylene compounds associated and remaining in the product as produced and used, and (ii) diluents or solvents, if any, used in the manufacture of the detergent either during or after its formation, but before addition of a carrier, if a carrier is employed.
• additives such as one or more fuel-soluble antioxidants, demulsifying agents; antioxidants, such as hindered phenols and amines; rust or corrosion inhibitors, metal deactivators, combustion modifiers, alcohol cosolvents, octane improvers, emission reducers, friction modifiers, lubricity additives, ancillary detergent/dispersant additives, markers, dyes and multifunctional additives (e.g., methylcyclopentadienyl manganese tricarbonyl and/or other cyclopentadienyl manganese tricarbonyl compounds) can also be included in the fuels and additive concentrates. These components can be present in the composition in any desired concentrations. For example, each component can be present in an amount at least sufficient for it to exert its intended function or functions in the finished fuel composition.
• the base fuels used in formulating the fuels disclosed herein can be any and all base fuels suitable for use in the operation of spark ignition internal combustion engines, such as unleaded motor and aviation gasolines, and so-called reformulated gasolines which often contain both hydrocarbons of the gasoline boiling range and fuel-soluble oxygenated blending components (“oxygenates”).
• suitable oxygenates include alcohols, such as methanol and ethanol; fuel-soluble ethers, such as methyl tertiary butyl ether, ethyl tertiary butyl ether, and methyl tertiary amyl ether; and mixtures of such materials.
• Oxygenates when used, can be present in the base fuel in any desired amount. Choosing an effective amount of oxygenates is within the ordinary skill of the art.
• Exact quantities of the starting materials were pre-determined and calculated based upon a mole ratio of 2:1:2 of 2-methyl-4-polyisobutyl phenol, dimethylaminepropylamine (DMAPA), and formaldehyde, respectfully.
• the 2-methyl-4-polyisobutyl phenol was added to a round bottom flask, followed by the addition of approximately 75% of the total calculated amount of Aromatic 100 solvent to be used during the process.
• the mixture was stirred under a nitrogen blanket. Once the mixture was homogeneous, the calculated amount of DMAPA was added. The temperature of the mixture was about 40 to 45° C. Formaldehyde was added, and the temperature of the mixture increased to about 45 to 50° C.
• the mixture was heated and distilled under nitrogen using a Dean Stark trap set to 150° C. During distillation, the temperature of 150° C. was maintained for about 2 to 2.5 hours. After distillation, sufficient Aromatic 100 solvent was added to the intermediate product to bring the final package composition to 25% solvent, taking into consideration the loss of water.
• Example 2 Gasoline fuel compositions employing the final product of Example 2 were subjected to engine tests whereby the substantial effectiveness of these compositions in reducing intake valve deposit weight was demonstrated.
• the above reaction products of Example 2 were compared with several other detergent compounds, including a first comparative compound formed by a mannich reaction of a 1:1:1 mole ratio of 2-methyl-4-polyisobutyl phenol, dibutylamine, and formaldehyde (“Mannich 1 additive”); a second comparative compound formed by a mannich reaction of a 1:1:1 mole ratio of 2-methyl-4-polyisobutyl phenol, DMAPA, and formaldehyde (“Mannich 2 additive”); and a third comparative compound that was a PIB Amine.
• the compounds of example 2 and the comparative compounds were each blended with a base fuel to form fuel compositions that are referred to in Table 1 and Table 2 by the additive compound employed (Example 2 Compounds, Mannich 1, Mannich 2, and PIB Amine
• a second comparative IVD Engine test of the compounds of Example 2; Mannich 1, Mannich 2, PIB Amine and the base fuel without additive was run using an IVD Bench Simulator (Model L-2), which can be used to test gasoline detergent IVD performance.
• the test simulates the IVD deposition in an engine.
• the fuel compositions with detergent additives were run through an injector.
• a separate air flow was run through an air flow line to the injector.
• the air flow and gasoline flow were mixed at the tip of the injector, and the mixture was directed against a heated metal plate. Plate temperatures were controlled at around 174° C. Gasoline evaporated on the surface of the hot plate, leaving a deposit and stain behind.

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  • 2006-08-17 US US11/465,278 patent/US20080040968A1/en not_active Abandoned
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