Patents Represented by Attorney Fred R. Ahlers
  • Patent number: 4029592
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when such polybutenes contain rather small amounts, i.e., 5 to 200 ppm, of halogenated, preferably chlorinated and/or brominated aliphatic or aromatic hydrocarbons. Preference is given to such halogen containing compounds having a sufficient vapor pressure at a temperature in the range of 100.degree. to 300.degree. C to be substantially completely removed at absolute pressures in the range of 5 to 760 mm Hg.
    Type: Grant
    Filed: December 5, 1975
    Date of Patent: June 14, 1977
    Assignee: Standard Oil Company (Indiana)
    Inventors: Imre Puskas, John A. Cengel
  • Patent number: 4028264
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when reacted in the presence of rather small amounts, i.e., 5 to 200 ppm, of alpha halogen-containing, preferably chlorine or bromine-containing, aliphatic or aromatic carbonyls including acetals as additives. Use of such halogen-containing additives in the addition reaction of polybutene with said unsaturated anhydrides can reduce formation of undesired tarry product resulting from polymerization and/or thermal decomposition of the unsaturated anhydrides.
    Type: Grant
    Filed: April 18, 1975
    Date of Patent: June 7, 1977
    Assignee: Standard Oil Company (Indiana)
    Inventors: Imre Puskas, John A. Cengel
  • Patent number: 4017548
    Abstract: A mixture of BF.sub.3 gas and vapors of an alkane hydrocarbon having a normal boiling point in the range of about 80.degree. to about 125.degree. C are recovered as exhaust from the partial-condensing zone of a stripping system to which is fed 6-25 weight percent of said alkane as a liquid dissolved in the fluid reaction mixture from BF.sub.3 -phenolate catalyzed alkylation of phenol with 500-3000 M.W. liquid viscous mono-olefinic polymer of propylene or butylene and BF.sub.3 -free portion of the fluid reaction mixture is withdrawn as liquid from the partial-reboiling zone of said system. The removal of BF.sub.3 by use of such stripping operation is successful without boiling a mixture of said alkane and said alkylation reaction mixture.
    Type: Grant
    Filed: October 6, 1975
    Date of Patent: April 12, 1977
    Assignee: Standard Oil Company (Indiana)
    Inventor: Dennis G. Petrille
  • Patent number: 4008168
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when such polybutenes contain rather small amounts, i.e., 5 to 200 ppm, of halogenated, preferably chlorinated and/or brominated carboxylic or sulfonic acid. Preference is given to such halogen containing compounds having a sufficient vapor pressure at a temperature in the range of 100.degree. to 300.degree. C to be substantially completely removed at absolute pressures in the range of 5 to 760 mm Hg. Use of such polybutenes containing such halogenated compounds in the addition reaction with said unsaturated anhydrides can reduce formation of undesired tarry product resulting from polymerization and/or thermal decomposition of the unsaturated anhydrides and enhance yield of desired alkenyl-substituted anhydride.
    Type: Grant
    Filed: November 19, 1975
    Date of Patent: February 15, 1977
    Assignee: Standard Oil Company (Indiana)
    Inventors: Imre Puskas, John A. Cengel
  • Patent number: 4005021
    Abstract: Oil-soluble products, suitable as dispersant additives for lubricants, are obtained by reacting (a) a high molecular weight olefin polymer, having an average molecular weight of at least about 600, with acrylonitrile, a halogen, e.g., chlorine, in the presence of a catalyst, e.g., iodine, (b) reacting the product of (a) with a primary aliphatic amine, (c) reacting the resultant product of (b) with maleic anhydride, and (d) reacting the product resulting from (c) with an aliphatic amine or polyamine containing at least one primary amino group per anhydride function on the product (c).
    Type: Grant
    Filed: March 26, 1975
    Date of Patent: January 25, 1977
    Assignee: Standard Oil Company (Indiana)
    Inventor: Richard J. Lee
  • Patent number: 3996285
    Abstract: Title compounds are novel oil-soluble, detergent-dispersant addition products for crankcase lubricating oils and are prepared by reacting a primary or secondary amine with 1-chloro-2-methylpropenyl substituted alkane hydrocarbons, especially 1-chloro-2-methylpropenyl terminated butene polymers, having a total of 20 to 180 carbon atoms.
    Type: Grant
    Filed: April 17, 1975
    Date of Patent: December 7, 1976
    Inventor: George S. Culbertson
  • Patent number: 3985802
    Abstract: Oil soluble high molecular weight Mannich condensation products formed by reacting (1) high molecular weight alkyl-substituted hydroxy aromatic compounds whose alkyl-substituent has a number average molecular weight (Mn) from about 600-100,000, (2) a compound containing at least one HN < group, and (3) an aldehyde in the respective molar reactant ratio of 1:0.1-10:1.0-10, are highly efficient ashless type (metal free) dispersant-detergent lubricant oil addition agents. Lubricating oils containing these compositions provide a high degree of protection against the deposition of sludge and varnish and corrosion when used as crankcase lubricants. Bis-Mannich products prepared by condensing (1) a 850-2500 Mn polyalkyl-substituted phenol, (2) an alkylene polyamine and (3) formaldehyde in the respective molar ratio of 1.0:0.7-1.0:1.5-2.
    Type: Grant
    Filed: October 8, 1974
    Date of Patent: October 12, 1976
    Assignee: Standard Oil Company (Indiana)
    Inventors: Edmund J. Piasek, Robert E. Karll
  • Patent number: 3985672
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when such polybutenes contain rather small amounts, i.e., 5 to 200 ppm, of brominated dialkylhydantoin. Preference is given to such bromine containing compounds having a sufficient vapor pressure at a temperature in the range of 100.degree. to 300.degree.C. to be substantially completely removed at absolute pressures in the range of 5 to 760 mm Hg. Use of such polybutenes containing such brominated compounds in the addition reaction with said unsaturated anhydrides can reduce formation of undesired tarry product resulting from polymerization and/or thermal decomposition of the unsaturated anhydrides and enhance yield of desired alkenyl-substituted anhydride.
    Type: Grant
    Filed: May 19, 1975
    Date of Patent: October 12, 1976
    Assignee: Standard Oil Company (Indiana)
    Inventors: John A. Cengel, Imre Puskas
  • Patent number: 3960900
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxlyic acids when such polybutenes contain rather small amounts, i.e., 5 to 200 ppm, of halogenated, preferably chlorinated and/or brominated aliphatic or aromatic hydrocarbons. Preference is given to such halogen containing compounds having a sufficient vapor pressure at a temperature in the range of 100.degree. to 300.degree.C to be substantially completely removed at absolute pressures in the range of 5 to 760 mm Hg.
    Type: Grant
    Filed: May 10, 1973
    Date of Patent: June 1, 1976
    Assignee: Standard Oil Company
    Inventors: Imre Puskas, John A. Cengel
  • Patent number: 3960865
    Abstract: Title compounds are novel oil-soluble, detergent-dispersant addition products for crankcase lubricating oils and are prepared by reacting a primary or secondary amine with 1-chloro-2-methylpropenyl substituted alkane hydrocarbons, especially 1-chloro-2-methylpropenyl terminated butene polymers, having a total of 20 to 180 carbon atoms.
    Type: Grant
    Filed: April 17, 1975
    Date of Patent: June 1, 1976
    Assignee: Standard Oil Company
    Inventor: George S. Culbertson
  • Patent number: 3954812
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when such polybutenes contain rather small amounts, i.e., 5 to 200 ppm, of halogenated, preferably chlorinated and/or brominated carboxylic or sulfonic acid. Preference is given to such halogen containing compounds having a sufficient vapor pressure at a temperature in the range of 100.degree. to 300.degree.C to be substantially completely removed at absolute pressures in the range of 5 to 760 mm Hg. Use of such polybutenes containing such halogenated compounds in the addition reaction with said unsaturated anhydrides can reduce formation of undesired tarry product resulting from polymerization and/or thermal decomposition of the unsaturated anhydrides and enhance yield of desired alkenyl-substituted anhydride.
    Type: Grant
    Filed: May 10, 1973
    Date of Patent: May 4, 1976
    Assignee: Standard Oil Company
    Inventors: Imre Puskas, John A. Cengel
  • Patent number: 3953348
    Abstract: Novel addition agents for lubricants, are obtained by reacting a high molecular weight olefin polymer, having an average molecular weight of at least about 600, with acetonitrile and a halogen, for example chlorine, in the presence of a catalyst, such as iodine, for example, to form the intermediate A which is then reacted with a piperazine or aminoalkyl-substituted piperazine.
    Type: Grant
    Filed: March 3, 1975
    Date of Patent: April 27, 1976
    Assignee: Standard Oil Company
    Inventor: Richard J. Lee
  • Patent number: 3953349
    Abstract: Novel addition agents for lubricants, are obtained by reacting a high molecular weight olefin polymer, having an average molecular weight of at least about 600, with acetonitrile and a halogen, for example chlorine, in the presence of a catalyst, such as iodine, for example, to form the intermediate (A) which is reacted with a primary or secondary amine.
    Type: Grant
    Filed: March 3, 1975
    Date of Patent: April 27, 1976
    Assignee: Standard Oil Company
    Inventor: Richard J. Lee
  • Patent number: 3953475
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to 3000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when reacted in the presence of rather small amounts, i.e., 5 to 200 ppm, of alpha halogen-containing, preferably chlorine or bromine-containing, aliphatic or aromatic carbonyls including acetals as additives. Use of such halogen-containing additives in the addition reaction of polybutene with said unsaturated anhydrides can reduce formation of undesired tarry product resulting from polymerization and/or thermal decomposition of the unsaturated anhydrides.
    Type: Grant
    Filed: May 10, 1973
    Date of Patent: April 27, 1976
    Assignee: Standard Oil Company
    Inventors: Imre Puskas, John A. Cengel
  • Patent number: 3951977
    Abstract: Title compounds are 4-[alkyl-substituted carbophenoxy] phthalic anhydride, acid, mono- and diesters, mono- and diamines and imides. These compounds are obtained by reaction of water, alcohols, amino-alcohols and nitrogen-containing compounds having at least one HN< group with 4-[alkyl-substituted carbophenoxy] phthalic anhydride which can be obtained by the reaction of a 4-acid halide of trimellitic anhydride with an alkyl-substituted phenol wherein the alkyl-substituent has thirty or more carbon atoms. The title compounds are soluble in mineral oil and function therein as anti-wear, anti-rust or dispersant-detergent addition agents.
    Type: Grant
    Filed: September 16, 1970
    Date of Patent: April 20, 1976
    Assignee: Standard Oil Company
    Inventors: Edmund J. Plasek, Imre Puskas
  • Patent number: 3950426
    Abstract: Title compounds are novel oil-soluble, detergent-dispersant addition products for crankcase lubricating oils and are prepared by reacting a primary or secondary amine with 1-chloro-2-methylpropenyl substituted alkane hydrocarbons, especially 1-chloro-2-methylpropenyl terminated butene polymers, having a total of 20 to 180 carbon atoms.
    Type: Grant
    Filed: August 27, 1973
    Date of Patent: April 13, 1976
    Assignee: Standard Oil Company
    Inventor: George S. Culbertson
  • Patent number: 3947494
    Abstract: Phthalic acids of improved quality are obtained direct from oxidation of xylenes with molecular oxygen in oxidation zone having small amounts of haloacetic acid present in liquid phase acetic acid solution of one or more heavy metal oxidation catalyst and bromide ion releasing bromine-containing compound. Particularly useful haloacetic acids are those having aqueous dissociation constant K.sub.A greater than 1.0 .times. 10.sup..sup.-3. Such quality improvement is manifested by decrease in carboxybenzaldehyde and toluic acid impurity contents and/or metal salt content.
    Type: Grant
    Filed: December 20, 1972
    Date of Patent: March 30, 1976
    Assignee: Standard Oil Company
    Inventor: George E. Kuhlmann
  • Patent number: 3944601
    Abstract: Phthalic acids of improved quality are obtained direct from oxidation of xylenes with molecular oxygen in oxidation zone having less than one equivalent of strongly acidic inorganic acid per equivalent of catalyst metal present in addition to a liquid phase acetic acid solution of one or more heavy metal oxidation catalyst and bromine releasing bromide compound. Particularly useful inorganic acids are those having ionization constant K.sub.A greater than 1.0 .times. 10.sup.-.sup.2, e.g. hydrobromine, nitric, sulfuric and phosphoric acids. Such quality improvement is manifested by decreased aldehydic acid and toluic acid impurity contents.
    Type: Grant
    Filed: December 20, 1972
    Date of Patent: March 16, 1976
    Assignee: Standard Oil Company
    Inventor: George E. Kuhlmann
  • Patent number: 3941834
    Abstract: Aliphatic hydrocarbon-substituted sulfonic acids, sulfonyl chlorides, amino sulfonic acids, sulfonamides and alkaline earth metal salts of such acids whose hydrocarbon substituent has an average molecular weight in the range of 300 to 200,000 are novel, useful compounds readily prepared through reaction of chlorosulfonic acid with a polymeric hydrocarbon having at least one carbon to carbon double bond as in the liquid to solid polypropene and polybutene or copolymer of two or more C.sub.2 to C.sub.6 unsaturated hydrocarbons having said average molecular weight. Such sulfonic acids, sulfonyl chlorides, amino sulfonic acids, sulfonamides and alkaline earth metal salts of the acid are soluble in hydrocarbon feeds (i.e., gasoline, diesel and heating fuels) and in lubricating oils as are the alkaline earth metal salts of such acids.
    Type: Grant
    Filed: June 9, 1971
    Date of Patent: March 2, 1976
    Assignee: Standard Oil Company
    Inventor: Richard J. Lee
  • Patent number: 3935249
    Abstract: Viscous polybutenes of number average molecular weight (M.sub.n) in the range of about 300 to about 3,000 have improved reactivity with intramolecular anhydrides of unsaturated aliphatic dicarboxylic acids when reacted in the presence of rather small amounts, i.e., 5 to 200 ppm, of inorganic halogen preferably chlorine and/or bromine containing compounds. Use of such halogen containing compounds in the addition reaction of polybutene with said unsaturated anhydrides can reduce formation of undesired tarry product resulting from polymerization and/or thermal decomposition of the unsaturated anhydrides.
    Type: Grant
    Filed: May 10, 1973
    Date of Patent: January 27, 1976
    Assignee: Standard Oil Company
    Inventors: Imre Puskas, John A. Cengel