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Oxazoline derivatives as additives useful in oleaginous compositions

Assignee: ExxonMobil Technology and Engineering Co
•
Filing: 1975-01-23
•
Granted: 1977-09-20
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Expires: 1995-01-23
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Abstract

Abstract Derivatives of Oxazoline reaction products of hydrocarbon substituted dicarboxylic acid, ester, or anhydride, for example octadecenylsuccinic anhydride and polyisobutenylsuccinic anhydride with 2,2-disubstituted-2-amino-1-alkanols, such as tris-hydroxymethylaminomethane (THAM) are useful additives in oleaginous compositions, such as sludge dispersants for lubricating oil, or anti-rust agents for gasoline.

Inventors

  • 👤 Jack Ryer
  • 👤 James Zielinski
  • 👤 Harold N. Miller
  • 👤 Stanley J. Brois

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 12:24
CPC Classifications
C; C10; C10M; C10M1/00; C10M1/08; C07; C07D; C07D263/00; C07D263/02; C07D263/08; C07D263/10; C07D263/12; C07D263/14; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6527; C07F9/653; C08; C08F; C08F8/00; C08F8/30; C08F8/32; C08G; C08G63/00; C08G63/68; C08G63/685; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221; C10L1/232; C10L1/233; C10L1/234; C10L1/238; C10L1/26; C10L1/2691; C10L1/30; C10L1/301; C10L1/303; C10M2205/00; C10M2205/02; C10M2205/022; C10M2205/026; C10M2205/14; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/027; C10M2207/028; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/122; C10M2207/123; C10M2207/125; C10M2207/129; C10M2207/22; C10M2207/28; C10M2207/282; C10M2207/32; C10M2207/34; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/086; C10M2209/10; C10M2209/103; C10M2209/109; C10M2209/11; C10M2209/112; C10M2211/00; C10M2211/02; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/086; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/045; C10M2223/06; C10M2223/061; C10M2223/065; C10M2223/08; C10M2223/12; C10M2225/00; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/06; C10M2227/061; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/02; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/08; C10N2040/12; C10N2040/13; C10N2040/135; C10N2040/25; C10N2040/252; C10N2040/253; C10N2050/00; C10N2050/10; C10N2070/00; C10N2070/02

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 327 words
A composition comprising a major amount of a liquid hydrocarbon of the class consisting essentially of fuels and lubricating oils and a minor but dispersing amount of a liquid hydrocarbon soluble derivative of the oxazoline reaction product of a substantially saturated aliphatic hydrocarbyl substituted C 4 -C 10 mono-unsaturated dicarboxylic acid material selected from the group consisting of acids, acid anhydrides and esters having at least about 8 carbon atoms in said hydrocarbyl group with from at least 1 to about 2 mole equivalent, per moel equivalent of said dicarboxylic acid material, of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons, and which is represented by the formula: ##STR7## wherein X is an alkyl or hydroxyl alkyl group, with at least one of the X substituents being a hydroxyl alkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3, said reaction conditions being at a temperature of from about 140° to 240° C. for from 1/2 to 24 hours whereby at least one carboxylic acyl group is converted into an oxazoline ring, said reaction product being derivatized by reaction with a member of the group consisting of: a. an aliphatic, saturated amine containing 2 to 60 carbon atoms and 1 to 12 nitrogen atoms and of the general formulae: ##STR8## wherein R, R' and R" are independently selected from the group consisting of hydrogen; C 1 to C 12 straight or branched chain alkyl radicals; C 1 to C 12 alkoxy substituted C 2 to C 6 alkylene radicals; C 2 to C 12 hydroxy or amino alkylene radicals; and C 1 to C 12 alkylamino substituted C 2 to C 6 alkylene radicals; s is 2 to 6 and, t is 0 to 10; and, b. a polyol selected from the group consisting of diethylene glycol, pentaerythritol, trimethylol propane, ethylene glycol, propylene glycol, glycol ethyl ether and diethylene glycol ethyl ether.
Claim 2
Dependent Claim 327 words
A composition comprising a major amount of a liquid hydrocarbon of the class consisting essentially of fuels and lubricating oils and a minor but dispersing amount of a liquid hydrocarbon soluble derivative of the oxazoline reaction product of a substantially saturated aliphatic hydrocarbyl substituted C 4 -C 10 mono-unsaturated dicarboxylic acid material selected from the group consisting of acids, acid anhydrides and esters having at least about 8 carbon atoms in said hydrocarbyl group with from at least 1 to about 2 mole equivalent, per moel equivalent of said dicarboxylic acid material, of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons, and which is represented by the formula: ##STR7## wherein X is an alkyl or hydroxyl alkyl group, with at least one of the X substituents being a hydroxyl alkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3, said reaction conditions being at a temperature of from about 140° to 240° C. for from 1/2 to 24 hours whereby at least one carboxylic acyl group is converted into an oxazoline ring, said reaction product being derivatized by reaction with a member of the group consisting of: a. an aliphatic, saturated amine containing 2 to 60 carbon atoms and 1 to 12 nitrogen atoms and of the general formulae: ##STR8## wherein R, R' and R" are independently selected from the group consisting of hydrogen; C 1 to C 12 straight or branched chain alkyl radicals; C 1 to C 12 alkoxy substituted C 2 to C 6 alkylene radicals; C 2 to C 12 hydroxy or amino alkylene radicals; and C 1 to C 12 alkylamino substituted C 2 to C 6 alkylene radicals; s is 2 to 6 and, t is 0 to 10; and, b. a polyol selected from the group consisting of diethylene glycol, pentaerythritol, trimethylol propane, ethylene glycol, propylene glycol, glycol ethyl ether and diethylene glycol ethyl ether.
Claim 3
Dependent Claim 53 words
A composition according to claim 1, wherein said oxazoline reaction product is the mono-oxazoline product of an alkenyl succinic anhydride or acid which has been reacted with about one mole equivalent of trishydroxy methyl aminomethane, said alkenyl substituent having a number average molecular weight within the range of about 1000 and about 20,000.
Claim 4
Dependent Claim 67 words
A composition according to claim 1 wherein said oxazoline reaction product is the mono-oxazoline product of hydrocarbon substituted succinic anhydride reacted with about one mole equivalent of tris-hydroxymethylaminomethane, said mono-oxazoline being further derivatized by reaction with about a molar proportion of an alkylene polyamine containing 2 to 12 nitrogen atoms, and wherein pairs of nitrogen atoms are joined by alkylene groups of 2 to 4 carbon atoms.
Claim 5
Dependent Claim 27 words
A composition according to claim 1, wherein said oil material is gasoline, said hydrocarbon contains about 12 to 49 carbon atoms and said polyol is diethylene glycol.
Claim 6
Dependent Claim 16 words
A composition according to claim 4, wherein said hydrocarbon substituted succinic anhydride is octadecenyl succinic anhydride.
Claim 7
Dependent Claim 42 words
An oleaginous composition according to claim 1, wherein said oily material is a mineral lubricating oil, and the amount of said reaction product is in the range of about 0.01 to 10 wt. %, based on the total weight of said composition.
Claim 8
Dependent Claim 33 words
An oleaginous composition according to claim 1, wherein said material is a hydrocarbon fuel containing about 0.001 to 0.5 wt. %, based on the weight of the total composition, of said reaction product.
Claim 9
Dependent Claim 11 words
A composition according to claim 7, wherein said fuel is gasoline.
Claim 10
Dependent Claim 220 words
A composition comprising a major amount of a liquid hydrocarbon of the class consisting essentially of fuels and lubricating oils and a minor but dispersing amount of a liquid hydrocarbon soluble derivative of the oxazoline reaction product of a polyisobutylene substituted C 4 -C 10 mono-unsaturated dicarboxylic acid material selected from the group consisting of acids, acid anhydrides and esters with from at least 1 to about 2 mole equivalent, per mole equivalent of said dicarboxylic acid material, of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons, and which is represented by the formula: ##STR9## wherein X is an alkyl or hydroxyl alkyl group, with at least one of the X substituents being a hydroxyl alkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3, said reaction conditions being at a temperature of from about 140° C. to 240° C. for from 1/2 to 24 hours whereby at least one carboxylic acyl group is converted into an oxazoline ring, said reaction product being derivatized by reaction with an alkylene polyamine containing 2 to 12 nitrogen atoms and wherein pairs of nitrogen atoms are joined by alkylene groups of 2 to 4 carbon atoms, said polyisobutylene substituent having a molecular weight of from 900 to 3000.
Claim 11
Dependent Claim 220 words
A composition comprising a major amount of a liquid hydrocarbon of the class consisting essentially of fuels and lubricating oils and a minor but dispersing amount of a liquid hydrocarbon soluble derivative of the oxazoline reaction product of a polyisobutylene substituted C 4 -C 10 mono-unsaturated dicarboxylic acid material selected from the group consisting of acids, acid anhydrides and esters with from at least 1 to about 2 mole equivalent, per mole equivalent of said dicarboxylic acid material, of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons, and which is represented by the formula: ##STR9## wherein X is an alkyl or hydroxyl alkyl group, with at least one of the X substituents being a hydroxyl alkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3, said reaction conditions being at a temperature of from about 140° C. to 240° C. for from 1/2 to 24 hours whereby at least one carboxylic acyl group is converted into an oxazoline ring, said reaction product being derivatized by reaction with an alkylene polyamine containing 2 to 12 nitrogen atoms and wherein pairs of nitrogen atoms are joined by alkylene groups of 2 to 4 carbon atoms, said polyisobutylene substituent having a molecular weight of from 900 to 3000.
Claim 12
Dependent Claim 12 words
A composition according to claim 9, wherein said amine is tetraethylene pentamine.

References Cited (Backward Citations)

US2636038A Cited
US2897182A Cited
US3329658A Cited
US3184474A Cited
US3516944A Cited
US3966620A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-09-19 1981-03-21 1981-09-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-09-19 1985-03-21 1985-09-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-09-19 1989-03-21 1989-09-20 $7700.00 Window Closed / Lapsed

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