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US3868330A Expired / Lapsed US ⏱️ 0.0 years remaining

Lubricants and fuel containing high molecular weight carboxylic acid acylating agents and their derivatives

Assignee: Lubrizol Corp
•
Filing: 1973-05-16
•
Granted: 1975-02-25
•
Expires: 1993-05-16
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Abstract

Abstract Process for preparing high molecular weight polycarboxylic acid acylating agents by contacting chlorine with a reaction mixture comprising (1) high molecular weight monocarboxylic acid and ethylenically unsaturated low molecular weight mono- or polycarboxylic acid acylating agent or (2) high molecular weight aliphatic hydrocarbon, ethylenically unsaturated low molecular weight mono-carboxylic acid acylating agent, and ethylenically unsaturated low molecular weight polycarboxylic acid acylating agent. Acylating agents thus produced have utility, for example, as intermediates in the preparation of acylated nitrogen compounds, esters, metal salts, and the like which are useful as additives in lubricants and fuels.

Inventors

  • 👤 Norman A Meinhardt
  • 👤 Charles Wesley Adams

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 09:56
CPC Classifications
C; C10; C10M; C10M1/00; C10M1/08; C08; C08F; C08F8/00; C08F8/18; C08F8/20; C08F8/22; C08F8/46; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/143; C10L1/18; C10L1/1817; C10L1/20; C10L1/206; C10L1/22; C10L1/221; C10L1/208; C10L1/24; C10L1/2493; C10M2203/00; C10M2203/02; C10M2203/022; C10M2203/024; C10M2203/04; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/024; C10M2205/026; C10M2207/00; C10M2207/28; C10M2207/282; C10M2207/34; C10M2207/40; C10M2207/402; C10M2207/404; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/10; C10M2209/103; C10M2209/104; C10M2209/105; C10M2209/106; C10M2209/108; C10M2209/109; C10M2209/11; C10M2209/111; C10M2211/00; C10M2211/04; C10M2211/044; C10M2211/06; C10M2211/08; C10M2213/00; C10M2213/02; C10M2213/04; C10M2213/06; C10M2213/062; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/044; C10M2215/06; C10M2215/064; C10M2215/066; C10M2215/08; C10M2215/082; C10M2215/086; C10M2215/10; C10M2215/102; C10M2215/12; C10M2215/14; C10M2215/18; C10M2215/22; C10M2215/221; C10M2215/222; C10M2215/223; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/024; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/06; C10M2219/062; C10M2219/064; C10M2219/066; C10M2219/068; C10M2219/08; C10M2219/082; C10M2219/083; C10M2219/087; C10M2219/088; C10M2219/089; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/045; C10M2223/06; C10M2223/065; C10M2223/12; C10M2223/121; C10M2225/00; C10M2225/02; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/02; C10M2227/04; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/041; C10M2229/042; C10M2229/043; C10M2229/044; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2010/06; C10N2010/08; C10N2010/14; C10N2010/16

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 375 words
A LUBRICANT OR FUEL COMPOSITION COMPRISING, RESPECTIVELY, A MAJOR AMMOUNT OF LUBRICATING OIL OR A NORMALLY LIQUID FUEL AND 0.0001% TO 20% BY WEIGHT OF AT LEAST ONE OIL-SOLUBLE HIGH MOLECULAR WEIGHT CARBOXYLIC ACID ACYLATING AGENT PREPARED BY A PROCESS COMPRISING INTIMATELY CONTACTING CHLORINE WITH A REACTION MIXTURE AT A TEMPERATURE OF AT LEAST 140*C. AND UP TO THE DECOMPOSITION TEMPERATURE, SAID REACTION MIXTURE BEING SELECTED FROM THE GROUP CONSISTING OF: I. A FIRST REACTANT WHICH IS AT LEAST ONE (A) MONOCARBOXYLIC ACID ACYLATING AGENT CONTAINING AN AVERAGE OF AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS IN THE ACYL MOIETY EXCLUSIVE OF THE CARBOXYL FUNCTIONS ANDAT LEAST ONE (B) LOW MOLECULAR WEIGHT CARBOXYLIC ACID REACTANT WHICH IS AN ETHYLENICALLY UNSATURATED MONO- OR POLYCARBOXYLIC ACID ACYLATING AGENT CONTAINING A TOTAL OF UP TO ABOUT TWENTY CARBON ATOMS IN THE ACRYL MOIETY, THE MOLE RATIO OF (A) TO (B) BEING SUCH THAT THERE IS AT LEAST 0.5 MOLE OF (B) FOR EACH MOLE OF (A) WITH THE PROVISO THAT (B) PROVIDES A MINIMUM OF ONE EQUIVALENT OF CARBOXYLIC ACID REACTANT IN THE REACTION MIXTURE PER MOLE OF (A); OR II. AT LEAST ONE (C) ETHYLENICALLY UNSTAURATED ALIPHATIC HYDROCARBON OR SUBSTITUTED ALIPHATIC HYDROCARBN REACTANT CONTAINING AN AVERAGE OF AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS, AT LEAST ONE (D) LOW MOLECULAR WEIGHT MONOCARBOXLIC ACID REACTANT WHICH IS AN ETHYLENICALLY UNSATURATED MONOCARBOCYLIC ACID ACYLATING AGENT CONTAINING UP TO ABOUT 20 CARBON ATOMS IN THE ACYL MOIETY, AND AT LEAST ONE (E) LOW MOLECULAR WEIGHT POLYCARBOXYLIC ACID REACTANT WHICH IS AN ETHYLENICALLY UNSATURATURED POLYCARBOXYLIC ACID ACYLATING AGENT CONTAINING UP TO ABOUT 20 CARBON ATOMS IN THE ACYL MOIETY, THE MOLE RATIO OF (C): (D): (E) BEING SUCH THAT THERE IS AT LEAST ABOUT 0.5 MOLE OF EACH OF (D) AND (E) PER MOLE OF (C) WITH THE PROVISO THAT THE COMBINED AMOUNT OF (D) AND (E) PROVIDES A MINUMUM OF AT LEAST TWO EQUIVALENTS OF LOW MOLECULAR WEIGHT MONOAND POLYYCARBOXYLIC ACID REACTANTS PER MOLE OF (C), THE TOTAL AMOUNT OF CHLORINE EMPOLYED IN SAID PROCESS BEING SUFFICIENT TO PROVIDE A T LEAST ABOUT 0.8 MOLE OF CHLORINE PER MOLE OF (B) OR AT LEAST ABOUT 0.8 MOLE OF CHLORINE PER THE TOTA NUMBER OF MOLES OF (D) AND (E), RESPECTIVELY.
Claim 2
Dependent Claim 375 words
A LUBRICANT OR FUEL COMPOSITION COMPRISING, RESPECTIVELY, A MAJOR AMMOUNT OF LUBRICATING OIL OR A NORMALLY LIQUID FUEL AND 0.0001% TO 20% BY WEIGHT OF AT LEAST ONE OIL-SOLUBLE HIGH MOLECULAR WEIGHT CARBOXYLIC ACID ACYLATING AGENT PREPARED BY A PROCESS COMPRISING INTIMATELY CONTACTING CHLORINE WITH A REACTION MIXTURE AT A TEMPERATURE OF AT LEAST 140*C. AND UP TO THE DECOMPOSITION TEMPERATURE, SAID REACTION MIXTURE BEING SELECTED FROM THE GROUP CONSISTING OF: I. A FIRST REACTANT WHICH IS AT LEAST ONE (A) MONOCARBOXYLIC ACID ACYLATING AGENT CONTAINING AN AVERAGE OF AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS IN THE ACYL MOIETY EXCLUSIVE OF THE CARBOXYL FUNCTIONS ANDAT LEAST ONE (B) LOW MOLECULAR WEIGHT CARBOXYLIC ACID REACTANT WHICH IS AN ETHYLENICALLY UNSATURATED MONO- OR POLYCARBOXYLIC ACID ACYLATING AGENT CONTAINING A TOTAL OF UP TO ABOUT TWENTY CARBON ATOMS IN THE ACRYL MOIETY, THE MOLE RATIO OF (A) TO (B) BEING SUCH THAT THERE IS AT LEAST 0.5 MOLE OF (B) FOR EACH MOLE OF (A) WITH THE PROVISO THAT (B) PROVIDES A MINIMUM OF ONE EQUIVALENT OF CARBOXYLIC ACID REACTANT IN THE REACTION MIXTURE PER MOLE OF (A); OR II. AT LEAST ONE (C) ETHYLENICALLY UNSTAURATED ALIPHATIC HYDROCARBON OR SUBSTITUTED ALIPHATIC HYDROCARBN REACTANT CONTAINING AN AVERAGE OF AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS, AT LEAST ONE (D) LOW MOLECULAR WEIGHT MONOCARBOXLIC ACID REACTANT WHICH IS AN ETHYLENICALLY UNSATURATED MONOCARBOCYLIC ACID ACYLATING AGENT CONTAINING UP TO ABOUT 20 CARBON ATOMS IN THE ACYL MOIETY, AND AT LEAST ONE (E) LOW MOLECULAR WEIGHT POLYCARBOXYLIC ACID REACTANT WHICH IS AN ETHYLENICALLY UNSATURATURED POLYCARBOXYLIC ACID ACYLATING AGENT CONTAINING UP TO ABOUT 20 CARBON ATOMS IN THE ACYL MOIETY, THE MOLE RATIO OF (C): (D): (E) BEING SUCH THAT THERE IS AT LEAST ABOUT 0.5 MOLE OF EACH OF (D) AND (E) PER MOLE OF (C) WITH THE PROVISO THAT THE COMBINED AMOUNT OF (D) AND (E) PROVIDES A MINUMUM OF AT LEAST TWO EQUIVALENTS OF LOW MOLECULAR WEIGHT MONOAND POLYYCARBOXYLIC ACID REACTANTS PER MOLE OF (C), THE TOTAL AMOUNT OF CHLORINE EMPOLYED IN SAID PROCESS BEING SUFFICIENT TO PROVIDE A T LEAST ABOUT 0.8 MOLE OF CHLORINE PER MOLE OF (B) OR AT LEAST ABOUT 0.8 MOLE OF CHLORINE PER THE TOTA NUMBER OF MOLES OF (D) AND (E), RESPECTIVELY.
Claim 3
Dependent Claim 14 words
A lubricant or fuel according to claim 1 wherein said reaction mixture is (I).
Claim 4
Dependent Claim 150 words
A lubricant or fuel composition according to claim 2 wherein (A) is at least one ethylenically unsaturated monocarboxylic acid acylating agent selected from the group consisting of the monocarboxylic acids per se, their corresponding anhydrides, acyl halides, esters derived from lower aliphatic monohydric alcohols of up to about seven carbon atoms selected from the lower alkanols, or mixtures of two or more of these ethylenically unsaturated monocarboxylic acylating agents, and wherein (B) is an Alpha , Beta -ethylenically unsaturated mono- or polycarboxylic acid acylating agent containing up to ten carbon atoms in the acyl moiety and selected from the group consisting of the carboxylic acids per se, their corresponding anhydrides, acyl halides, esters derived from lower aliphatic monohydric alcohols of up to about seven carbon atoms selected from the lower alkanols, and mixtures of two or more of these Alpha , Beta -ethylenically unsaturated mono- or polycarboxylic acid acylating agents.
Claim 5
Dependent Claim 86 words
A lubricant or fuel composition according to claim 3 wherein (A) is an aliphatic acylating agent having an average molecular weight within the range of about 700 to about 5,000 and being selected from the class consisting of the carboxylic acids per se, their anhydrides, their acyl chlorides, their lower alkyl esters derived from alkanols of up to four carbon atoms and mixtures of two or more of these, and wherein (B) is selected from the group consisting of aliphatic mono- or dicarboxylic acid acylating agents.
Claim 6
Dependent Claim 49 words
A lubricant or fuel composition according to claim 4 wherein (B) is selected from the group consisting of the carboxylic acids per se, their anhydrides, their acyl chlorides, their lower alkyl esters derived from alkanols of up to four carbon atoms, and mixtures of two or more of these.
Claim 7
Dependent Claim 34 words
A lubricant or fuel composition according to claim 5 wherein (B) is selected from the group consisting of acrylic acid, maleic acid, their anhydrides, their esters or mixtures of two or more of these.
Claim 8
Dependent Claim 15 words
A lubricant or fuel composition according to claim 1 wherein said reaction mixture is (II).
Claim 9
Dependent Claim 163 words
A lubricant or fuel composition according to claim 7 wherein (D) is at least one Alpha , Beta -ethylenically unsaturated monocarboxylic acid reactant containing up to ten aliphatic carbon atoms in the acyl moiEty and selected from the group consisting of the monocarboxylic acids per se, their corresponding anhydrides, acyl halides, esters derived from lower aliphatic monohydric alcohols of up to about seven carbon atoms selected from the lower alkanols, and mixtures of two or more of these Alpha , Beta -ethylenically unsaturated monocarboxylic acid reactants, and wherein (B) is at least one Alpha , Beta -ethylenically unsaturated polycarboxylic acid reactant containing up to ten carbon atoms in the acyl moiety and selected from the group consisting of the polycarboxylic acids per se, their corresponding anhydrides, acyl halides, esters derived from lower aliphatic monohydric alcohols of up to about seven carbon atoms selected from the lower alkanols, and mixtures of two or more of these Alpha , Beta -ethylenically unsaturated polycarboxylic acid reactants.
Claim 10
Dependent Claim 23 words
A lubricant or fuel composition according to claim 8 wherein (C) has an average molecular weight of about 700 to about 100, 000.
Claim 11
Dependent Claim 57 words
A lubricant or fuel composition according to claim 9 wherein (E) is a dicarboxylic acid reactant and wherein (D) and (E) are each selected from the carboxylic acids per se, their anhydrides, their acyl chlorides, their lower alkyl esters derived from the alkanols of up to four carbon atoms, and mixtures of two or more of these.
Claim 12
Dependent Claim 75 words
A lubricant or fuel composition according to claim 10 wherein (C) is a 1-monoolefin polymer having an average molecular weight of about 700 to about 5,000; (D) is selected from the group consisting of acrylic acid, its lower alkyl esters, and mixtures of two or more of these; and wherein (E) is selected from the group consisting of maleic acid, its anhydride, the lower alkyl esters thereof, and mixtures of two or more of these.
Claim 13
Dependent Claim 126 words
A lubricant or fuel composition comprising, respectively, a major amount of a lubricating oil or a normally liquid fuel and 0.0001% to about 20% by weight of at least one oil-soluble derivative selected from the class consisting of esters, acylated nitrogen compounds, and metal salts of oil-soluble high molecular weight carboxylic acid acylating agents as described in claim 1 and a member selected from the group consisting of monohydric aliphatic and cycloaliphatic alcohols of up to about twenty carbon atoms; polyhydric alcohols having from 2 to 10 hydroxyl groups and up to 20 carbon atoms; hydroxyaromatic compounds selected from the group consisting of phenols and naphthols and hydroxybenzene compounds having 2 to 4 hydroxyl groups; primary and secondary amines characterized by a radical having the configuration
Claim 14
Dependent Claim 98 words
A lubricant or fuel composition comprising, respectively, a major amount of a lubricating oil or a normally liquid fuel and about 0.001% to about 20% by weight of at least one oil-soluble derivative selected from the class consisting of esters and acylated nitrogen compounds made from the oil-soluble high molecular weight carboxylic acid acylating agents as described in claim 5 and a member selected from the group consisting of polyhydric alkanols containing three to ten carbon atoms and having at least 3 hydroxy groups or alkylene polyamines or mixtures of two or more of these alkanols and polyamines.
Claim 15
Dependent Claim 97 words
A lubricant or fuel composition comprising, respectively, a major amount of a lubricating oil or a normally liquid fuel and about 0.001% to about 20% by weight of at least one oil-soluble derivative selected from the class consisting of esteRs and acylated nitrogen compounds made from the oil-soluble high molecular weight carboxylic acid acylating agents according to claim 8 and a member selected from the group consisting of polyhydric alkanols having three to ten carbon atoms and having at least 3 hydroxyl groups or alkylene polyamines and mixtures of two or more of these alkanols and polyamines.
Claim 16
Dependent Claim 16 words
A lubricant composition according to claim 1 wherein said lubricating oil is a mineral lubricating oil.
Claim 17
Dependent Claim 16 words
A lubricant composition according to claim 12 wherein said lubricating oil is a mineral lubricating oil.
Claim 18
Dependent Claim 15 words
A fuel composition according to claim 1 wherein said fuel is a petroleum distillate fuel.
Claim 19
Dependent Claim 15 words
A fuel composition according to claim 12 wherein said fuel is a petroleum distillate fuel.
Claim 20
Dependent Claim 71 words
A concentrate suitable for preparing a lubricant or fuel composition according to claim 1 comprising a substantially stable dispersion or solution of said at least one oil-soluble high molecular weight carboxylic acid acylating agent in a substantially inert nonpolar organic liquid, the amount of said at least one high molecular weight carboxylic acid acylating agent being such as to comprise from about 5% to about 90% by weight of said concentrate.
Claim 21
Dependent Claim 15 words
A fuel composition according to claim 12 wherein said fuel is a petroleum distillate fuel.

References Cited (Backward Citations)

US3215707A Cited
US3231587A Cited
US3639242A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-02-24 1978-08-26 1979-02-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-02-24 1982-08-26 1983-02-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-02-24 1986-08-26 1987-02-25 $7700.00 Window Closed / Lapsed

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