Patents by Inventor Kirkwood S. Cottman
Kirkwood S. Cottman has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5371289Abstract: The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula: ##STR1## comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula: ##STR2## and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula:R.sup.1 --NH.sub.2in the presence of methanol wherein R.sup.1 is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.Type: GrantFiled: March 22, 1993Date of Patent: December 6, 1994Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5310811Abstract: Free radically curable rubbers are crosslinked with the aid of a free radical initiator and a co-curing agent, which is an acrylate or methacrylate ester of a hydroxybenzene or hydroxynaphthalene compound containing two or more hydroxyl groups, at least two of which are esterified. The rubbers which are used in the present invention are natural rubber and synthetic rubbers derived from a diene monomer. Preferred co-curing agents are acrylate and methacrylate esters of hydroxybenzene compounds in which the ester contains two or three acrylate or methacrylate groups per molecule. The amount of co-curing agent may be about 1-50 parts by weight per one hundred parts by weight of rubber (phr). Outstanding abrasion resistance and air oven aging are observed.Type: GrantFiled: September 22, 1993Date of Patent: May 10, 1994Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Kevin L. Rollick
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Patent number: 5191083Abstract: This invention is directed to the preparation of polymerizable monomers that are prepared from 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl) benzene (m-TMI) and 1-(1-isocyanato-1-methylethyl)-4-(1-methylethenyl) benzene (p-TMI). The monomers prepared from m- and p-TMI can contain numerous chemical moieties, and when polymerized, produce polymers that have chemically bonded to the polymeric backbone the functional moiety. More specifically, these TMI derived monomers may contain chain breaking antioxidant moieties, peroxide decomposing antioxidant moieties, ultraviolet stabilizing moieties, triplet quenching moieties, and other chemical moieties that are useful in polymers.Type: GrantFiled: February 28, 1989Date of Patent: March 2, 1993Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Kirkwood S. Cottman, Dane K. Parker
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Patent number: 5093517Abstract: There is disclosed a method for making compounds such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) which comprises reacting an alkyl thiopropionate with a glycol at temperatures between 50.degree. C. and 180.degree. C. in the presence of a catalytic amount of a dialkyl tin oxide.Type: GrantFiled: March 9, 1987Date of Patent: March 3, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5068439Abstract: The present invention relates to a process for the preparation of a N-substituted phenylenediamine of the formula: ##STR1## comprising reacting N-phenylquinoneimine of the formula: ##STR2## with a primary amine of the formula:R--NH.sub.2 (III),wherein the molar ratio of II to III in the reaction mixture ranges from about 1:1 to 1:10; and wherein R is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6. The present process is characterized by its excellent yields of high purity N-substituted phenylenediamines.Type: GrantFiled: October 12, 1990Date of Patent: November 26, 1991Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 5053540Abstract: The present invention relates to a process for the preparation of a p-aminodiphenylamine comprising reacting N-phenylquinoneimine of the formula: ##STR1## with ammonia, ammonium hydroxide or mixtures thereof, wherein the molar ratio of N-phenylquinoneimine to NH.sub.3 in the reaction mixture ranges from about 1:1 to 1:80.Type: GrantFiled: March 8, 1990Date of Patent: October 1, 1991Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4968843Abstract: The present invention relates to a process for the preparation of a N-substituted phenylenediamine of the formula: ##STR1## comprising reacting N-phenylquinoneimine of the formula: ##STR2## with a primary amine of the formula:R--NH.sub.2 (III),wherein the molar ratio of II to III in the reaction mixture ranges from about 1:1 to 1:10; and wherein R is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6. The present process is characterized by its excellent yields of high purity N-substituted phenylenediamines.Type: GrantFiled: March 8, 1990Date of Patent: November 6, 1990Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4853478Abstract: This invention is directed to the preparation of polymerizable monomers that are prepared from 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl) benzene (m-TMI) and 1-(1-isocyanato-1-methylethyl)-4-(1-methylethenyl) benzene (p-TMI). The monomers prepared from m- and p-TMI can contain numerous chemical moieties, and when polymerized, produce polymers that have chemically bonded to the polymeric backbone the functional moiety. More specifically, these TMI derived monomers may contain chain breaking antioxidant moieties, peroxide decomposing antioxidant moieties, ultraviolet stabilizing moieties, triplet quenching moieties, and other chemical moieties that are useful in polymers.Type: GrantFiled: February 18, 1987Date of Patent: August 1, 1989Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Kirkwood S. Cottman, Dane K. Parker
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Patent number: 4847313Abstract: This invention is concerned with the prevention of gel formation in polymers. More specifically, this invention is directed to a unique combination of materials that greatly lessens the formation of gel in elastomers during processing and storage. The combination comprises a hindered phenolic antioxidant and an alkylated phenol/primary mercaptan/formaldehyde reaction product.Type: GrantFiled: March 28, 1988Date of Patent: July 11, 1989Assignee: The Goodyear Tire & Rubber CompanyInventors: Joel Muse, Donald C. Grimm, Jerry J. Dillon, Kirkwood S. Cottman, Calvin A. Bennett
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Patent number: 4829115Abstract: This invention is concerned with the stabilization of organic materials subject to oxidative degradation. The synergists of this invention possess organothioethyl alcohol segmers or moieties which enhance the antioxidative activity of phenolic and amine stabilizers. The invention is also concerned with compounds that contain an organothioethyl alcohol moiety and their use in oxidizable materials in combination with polymerizable and/or conventional antidegradants.Type: GrantFiled: March 3, 1988Date of Patent: May 9, 1989Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4714772Abstract: This invention is directed to the preparation of polymerizable monomers that are prepared from 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl) benzene (m-TMI) and 1-(1-isocyanato-1-methylethyl)-4-(1-methylethenyl) benzene (p-TMI). The monomers prepared from m- and p-TMI can contain numerous chemical moieties, and when polymerized, produce polymers that have chemically bonded to the polymeric backbone the functional moiety. More specifically, these TMI derived monomers may contain chain breaking antioxidant moieties, peroxide decomposing antioxidant moieties, ultraviolet stabilizing moieties, triplet quenching moieties, and other chemical moieties that are useful in polymers.Type: GrantFiled: December 16, 1985Date of Patent: December 22, 1987Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Kirkwood S. Cottman, Dane K. Parker
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Patent number: 4604417Abstract: There are disclosed polymerizable thioester synergists which have utility in enhancing the antioxidative activity of phenolic and amine stabilizers. The invention is also concerned with the thioesters themselves, their use in oxidizable organics, their combination with polymerizable and/or conventional antioxidants, and with polymers which contain these thioesters as physical admixtures or segmeric units of the polymer.Type: GrantFiled: December 10, 1984Date of Patent: August 5, 1986Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4604439Abstract: This invention is directed to the preparation of polymerizable monomers that are prepared from 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl) benzene (m-TMI) and 1-(1-isocyanato-1-methylethyl)-4-(1-methylethenyl) benzene (p-TMI). The monomers prepared from m- and p-TMI can contain numerous chemical moieties, and when polymerized, produce polymers that have chemically bonded to the polymeric backbone the functional moiety. More specifically, these TMI derived monomers may contain chain breaking antioxidant moieties, peroxide decomposing antioxidant moieties, ultraviolet stabilizing moieties, triplet quenching moieties, and other chemical moieties that are useful in polymers.Type: GrantFiled: May 28, 1985Date of Patent: August 5, 1986Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Kirkwood S. Cottman, Dane K. Parker
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Patent number: 4579911Abstract: There are disclosed polymers which have nonionic surfactant moieties pendant to the polymeric backbone which exhibit activated sulfur vulcanization, a process for their preparation, and mixtures of polymeric cure activators and elastomers.Type: GrantFiled: June 3, 1985Date of Patent: April 1, 1986Assignee: The Goodyear Tire & Rubber CompanyInventors: Richard M. D'Sidocky, Kirkwood S. Cottman, Joseph F. Geiser, Paul H. Sandstrom, Robert A. Smith
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Patent number: 4521559Abstract: Two antioxidants functioning by different mechanisms are combined chemically into one molecule, allowing optimization of their antioxidant properties.Type: GrantFiled: June 27, 1983Date of Patent: June 4, 1985Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4446264Abstract: Compounds prepared by reacting maleic anhydride, maleic acid or their esters with thiols; which exhibit a synergistic effect when combined with a phenolic antioxidant in the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oil, etc. are disclosed.Type: GrantFiled: April 15, 1982Date of Patent: May 1, 1984Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4414408Abstract: Two antioxidants functioning by different mechanisms are combined chemically into one molecule, allowing optimization of their antioxidant properties.Type: GrantFiled: February 16, 1982Date of Patent: November 8, 1983Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4394476Abstract: Esters of alkyl thiomercaptophenols, such as bis[2-(3,5-ditertiary butyl-4-hydroxyphenylthio)-1-methylethyl]thiodipropionate, used as antioxidants to stabilize polymers against oxidated degradation.Type: GrantFiled: July 9, 1982Date of Patent: July 19, 1983Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4311637Abstract: There is disclosed polyphenolic mercaptophenol type antioxidants, a method of preparing the antioxidants and to polymer compositions containing such polyphenolic mercaptophenol type antioxidants. In particular, polyphenolic antioxidants such as 2-(2-hydroxy-3-tertiary-butyl-5-methylbenzyl)-4-methyl-6-tertiary butyl phenyl 3-(4-hydroxyphenylthio)propionate.Type: GrantFiled: February 8, 1980Date of Patent: January 19, 1982Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: RE32618Abstract: Mercaptophenols are reacted with compounds containing olefinic unsaturation, or polycyclic olefins, or dihydroxy compounds to form phenolic antioxidants such as 3,8-bis(4-hydroxyphenylthio)-tricyclo[5.2.1.0..sup.2,6 ] decane; 1,4-bis[2-(4-hydroxyphenylthio)ethyl]benzene and age resistant polymers containing said antioxidants.Type: GrantFiled: April 18, 1986Date of Patent: March 1, 1988Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman