Patents by Inventor Henry S. Makowski

Henry S. Makowski 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).

  • Patent number: 4226751
    Abstract: The present invention relates to an improved process for forming fibers for fabrics from neutralized sulfonated thermoplastic polymers, and novel ionic polymer fiber compositions derived therefrom, wherein the neutralized sulfonated thermoplastic polymer is dissolved in a solvent, preferably a mixed solvent, consisting of a backbone solvent and a polar cosolvent and spun into fibers. The neutralized sulfonated thermoplastic polymer has about 10 to about 100 meq. SO.sub.3 H per 100 grams of sulfonated thermoplastic polymer, of which at least 95% is neutralized with a cation being selected from the group consisting essentially of antimony, iron, lead, aluminum, or Groups I-A, II-A, I-B or II-B of the Periodic Table of Elements and mixture thereof.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Henry S. Makowski
  • Patent number: 4222914
    Abstract: This invention relates to a process for the formation of a neutralized sulfonated polymer having about 10 to about 60 meq. sulfonate groups, wherein the sulfonate groups are neutralized with a zinc counterion. A cement of a polymer having olefinic functional groups and a non-reactive solvent is contacted with a sulfonated agent such as an acyl sulfate. The sulfonated polymer is then neutralized with a solution of zinc acetate dissolved in a solvent system of methanol alone or methanol and water, wherein the volume percent of methanol based on non-reactive solvent is less than about 10. A carboxylic acid can be then added to the cement of the neutralized sulfonated polymer thereby forming a zinc salt of the carboxylic acid in situ, wherein the zinc salt of the carboxylic acid is a preferential plasticizer for the zinc sulfonate groups. The Brookfield viscosity at 0.6 rpm at room temperature of the cement of the zinc neutralized sulfonated polymer is less than about 50,000 cps.
    Type: Grant
    Filed: March 23, 1979
    Date of Patent: September 16, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Robert R. Klein, Robert D. Lundberg, Jan Bock
  • Patent number: 4221712
    Abstract: This invention relates to an improved process for the formation of an improved gel-free neutralized sulfonated elastomeric polymer having about 10 to about 50 meq. unneutralized sulfonate groups, wherein the unneutralized sulfonate groups are neutralized with a metal counterion being selected from the group including lithium, sodium, potassium, cesium, barium, calcium, magnesium, zinc, lead, iron (II), copper (II), mercury (II), and nickel. A cement of an elastomeric polymer having olefinic functional groups dissolved in a non-reactive solvent is contacted with a sulfonating agent such as an acyl sulfate thereby sulfonating the elastomeric polymer, and the sulfonation reaction is subsequently quenched by the addition of isopropanol at a concentration level of about 5 to about 30 volume percent based on a volume of the non-reactive solvent.
    Type: Grant
    Filed: March 23, 1979
    Date of Patent: September 9, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Jan Bock, Robert D. Lundberg
  • Patent number: 4210568
    Abstract: This invention relates to improved polymeric compositions of metal, amine and ammonium neutralized sulfonated polymers which are preferentially plasticized with an N-substituted organic carbamate at a minimum critical concentration level of at least 1 part by weight based on 100 parts by weight of the neutralized polymer, wherein N-substituted organic carbamate has the general formula selected from the group of: ##STR1## wherein R.sub.1, and R.sub.2 are normal or branched chain alkyl, cycloalkyl, aryl, alkaryl, or arylalkyl groups such as ethyl, butyl, octadecyl, behenyl, phenyl, benzyl, and dodecylphenyl and R.sub.4 and R.sub.6 and either R.sub.1 or R.sub.2 must be a long chain, preferably linear, saturated group containing from about 10 to about 50 carbon atoms and R.sub.3 and R.sub.5 are di, tri, or tetrafunctional aliphatic, cycloaliphatic, aryl or alkaryl groups and m is 2, 3, or 4 and n is 2, 3 or 4.
    Type: Grant
    Filed: April 20, 1978
    Date of Patent: July 1, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Robert D. Lundberg, Robert R. Klein
  • Patent number: 4208310
    Abstract: This invention relates to elastomeric blend compositions of a neutralized sulfonated elastomeric polymer. The compositions include a major portion of a sulfonated elastomeric polymer and a minor proportion of a non-polar wax, wherein the resultant composition has both improved physical and rheological properties.
    Type: Grant
    Filed: March 12, 1979
    Date of Patent: June 17, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Jan Bock, Henry S. Makowski
  • Patent number: 4196236
    Abstract: A process is disclosed for fabricating a thermoplastic, which thermoplastic is either a thermoplastic ionomer or a multiphase graft or block copolymer of the ABA (AB).sub.n, or ##STR1## wherein n is greater than 1 and wherein the polymer blocks, A and B, are each thermoplastic resins having softening points substantially above room temperature with the B block being present in at least about 30 wt. % of the total polymer. The thermoplastic composition is first suspended in finely divided form in a liquid medium in a sufficient amount such that the solids content of the resulting suspension is in the range of from about 15 to about 75 wt. %. The liquid medium must be nonvolatile and must be capable of plasticizing the B block (or the backbone if the ionomer is employed) of the thermoplastic composition above the softening point of that block but must not be capable of plasticizing the A block to a substantial extent. The suspension is then applied as a coating to any desired surface, e.g.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: April 1, 1980
    Inventors: Robert D. Lundberg, Henry S. Makowski
  • Patent number: 4193901
    Abstract: An improved process for the sulfonation of an unsaturated elastomeric polymer to form a sulfonated elastomeric polymer, wherein a cement which contains an elastomeric polymer dissolved in a non-reactive solvent is contacted with a sulfonating agent at between about -100.degree. C. and +100.degree. C. for a period of time sufficient to result in the sulfonation of the elastomeric polymer wherein the improvement includes the use of a sulfonating agent which is formed from mixtures of a sulfur trioxide donor complexed with a Lewis base and a carboxylic acid anhydride ##STR1## or an acyl halide ##STR2## or with both, wherein R is selected from the group consisting of CH.sub.3 --, C.sub.2 H.sub.5 --, C.sub.3 H.sub.7 --, C.sub.4 H.sub.9 --, C.sub.5 H.sub.11, C.sub.6 H.sub.13 and C.sub.6 H.sub.5 and mixtures thereof. The molar ratio of ##STR3## and/or ##STR4## with the SO.sub.3 of the complex is at least 0.5.
    Type: Grant
    Filed: March 12, 1979
    Date of Patent: March 18, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Robert D. Lundberg, Jan Bock
  • Patent number: 4184988
    Abstract: An improved process for the sulfonation of an unsaturated elastomeric polymer to form a sulfonated elastomeric polymer, wherein a cement which contains an elastomeric polymer dissolved in a nonreactive solvent is contacted with a sulfonating agent at between about -100.degree. C. and +100.degree. C. for a period of time sufficient to result in sulfonation of the elastomeric polymer wherein the improvement includes the use of a sulfonating agent which is formed from mixtures of acyl sulfate ##STR1## with carboxylic acid anhydrides ##STR2## with carboxylic acid halides ##STR3## or with both, wherein R is selected from the group consisting of CH.sub.3 --, C.sub.2 H.sub.5 --, C.sub.3 H.sub.7 --, C.sub.4 H.sub.9 --, C.sub.5 H.sub.11, C.sub.6 H.sub.13 or C.sub.6 H.sub.5 and mixtures thereof. The molar ratio of ##STR4## is at least one.
    Type: Grant
    Filed: October 16, 1978
    Date of Patent: January 22, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Robert D. Lundberg, Jan Bock
  • Patent number: 4183406
    Abstract: Improvements in the treatment of wells that penetrate subterranean formations are accomplished through the use of a polymer solution which includes a neutralized ionomeric polymer dissolved in an organic solvent and a polar cosolvent. The polymer has a backbone that is substantially soluble in the organic solvent and pendant ionomeric groups that are substantially insoluble in the organic solvent. The polar cosolvent solubilizes the pendant ionomeric groups such that the polymer solution upon introduction into the well has a viscosity less than about 20,000 centipoises and upon mixing with water the polar cosolvent is taken up by the water causing the polymer to aggregate and increase in viscosity sufficient to form a plug. The polymer solution may be used in well drilling operations, well completion operations, and secondary recovery operations.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: January 15, 1980
    Assignee: Exxon Production Research Company
    Inventors: Robert D. Lundberg, Dennis E. O'Brien, Henry S. Makowski, Robert R. Klein
  • Patent number: 4179422
    Abstract: This invention relates to blend compositions of thermoplastic resins and a neutralized sulfonated elastomeric polymer and a hydroxyalkyl carboxylate ester wherein the resultant composition has both improved physical and rheological properties such as compression set for blends exhibiting elastomeric characteristics and impact strength for blends exhibiting thermoplastic characteristics.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: December 18, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Charles P. O'Farrell
  • Patent number: 4172820
    Abstract: The present invention relates to an improved process for forming fibers for fabrics from neutralized sulfonated thermoplastic polymers, and novel ionic polymer fiber compositions derived therefrom, wherein the neutralized sulfonated thermoplastic polymer is dissolved in a solvent, preferably a mixed solvent, consisting of a backbone solvent and a polar cosolvent and spun into fibers. The neutralized sulfonated thermoplastic polymer has about 10 to about 100 meq. SO.sub.3 H per 100 grams of sulfonated thermoplastic polymer, of which at least 95% is neutralized with a cation being selected from the group consisting essentially of antimony, iron, lead, aluminum, or Groups I-A, II-A, I-B or II-B of the Periodic Table of Elements and mixture thereof.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: October 30, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Henry S. Makowski
  • Patent number: 4169820
    Abstract: This invention relates to extrusion and injection moldable type elastomeric compositions having a viscosity at 200.degree. C. at 0.73 sec.sup.-1 of about 8.times.10.sup.4 to about 8.times.10.sup.5 poises. The compositions used for elastomeric articles include 100 parts of a neutralized sulfonated EPDM terpolymer; about 25 to about 150 parts per hundred of a non-polar process oil; about 50 to about 300 parts per hundred of a filler; and a preferential plasticizer at about 0 to about 50 parts per hundred based on 100 parts of the sulfonated elastomeric polymer. The composition may also include a crystalline polyolefinic thermoplastic at less than about 100 parts per hundred by weight.These blend compositions can be readily processed due to their superior rheological properties on conventional plastic fabrication equipment into elastomeric articles having excellent physical properties and desirable rubbery characteristics.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: October 2, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Jan Bock, Robert D. Lundberg, Henry S. Makowski
  • Patent number: 4160751
    Abstract: This invention relates to injection moldable type elastomeric compositions having a viscosity at 200.degree. C. at 0.73 sec.sup.-1 of less than about 8.times.10.sup.4 poises. The compositions used for elastomeric articles include 100 parts of a neutralized sulfonated EPDM terpolymer; about 25 to about 150 parts per hundred of a non-polar process oil; about 25 to about 200 parts per hundred of a filler; and a preferential plasticizer at about less than 50 parts per hundred based on 100 parts of the sulfonated elastomeric polymer. The composition may also include a crystalline polyolefinic thermoplastic at least than about 100 parts per hundred by weight.These blend compositions can be readily processed due to their superior rheological properties on conventional plastic fabrication equipment, especially on low pressure injection molding equipment into elastomeric articles having excellent physical properties and desirable rubbery characteristics.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: July 10, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Jan Bock, Robert D. Lundberg, Henry S. Makowski
  • Patent number: 4157432
    Abstract: A bulk sulfonation process for the preparation of sulfonated polymers from hydrocarbon polymers having olefinic unsaturation or aromatic moieties, or both, includes intimately mixing the polymer by mechanical means in the absence of a solvent for the polymers with a sulfonation reagent at a sufficient temperature and time to effect the desired degree of sulfonation. The sulfonated polymer may be recovered as the free sulfonic acid or neutralized ionically with a basic compound. Sulfonated polymers including a substantial proportion of aromatic moieties yield water-soluble or water-dispersible salts, useful as thickening and flocculating agents, when neutralized with ammonia monobasic cations or lower alkyl amines. These materials, however, when sulfonated at a low level, e.g. <10 mole SO.sub.3 per mole aromatic, behave like water insensitive thermoplastics.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: June 5, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Henry S. Makowski, Jan Bock, Thomas Zawadski
  • Patent number: 4153588
    Abstract: This invention relates to plasticized metal neutralized sulfonated EPDM terpolymers having at least 65 wt. % of ethylene in the backbone of the EPDM terpolymer and extended compositions of these metal neutralized sulfonated EPDM terpolymers having 100 parts of a neutralized sulfonated EPDM terpolymer; less than about 100 parts per hundred of a non-polar process oil; less than about 300 parts per hundred of a filler; and a preferential plasticizer at about less than 60 parts per hundred based on 100 parts of the sulfonated elastomeric polymer. These compositions can be readily processed due to their superior rheological properties on conventional plastic fabrication equipment, especially on low pressure injection molding and extrusion equipment into elastomeric articles having improved physical properties.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: May 8, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Robert R. Klein, Robert D. Lundberg
  • Patent number: 4147677
    Abstract: This invention relates to a process for first preparing a free flowing finely divided powder of a neutralized sulfonated elastomer and subsequently and optionally admixing said formed powder with other agents such as fillers and oils thereby providing free flowing powders capable of being subsequently fabricated into tough elastomeric objects. The neutralized sulfonated elastomeric polymer can be converted into a free flowing finely divided powder which does not agglomerate or cold flow under ambient conditions by a variety of processes, preferably by a grinding process conducted at low temperatures. The formed powder of the neutralized sulfonated elastomeric polymer is blended with at least one chemical additive into a homogeneous mixture, wherein the chemical additive is selected from the group including fillers, polyolefinic thermoplastics, non-polar backbone process oils, lubricants or a metallic oxide and mixtures thereof.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: April 3, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Henry S. Makowski, Jan Bock
  • Patent number: 4145379
    Abstract: The present invention relates to a process for improving the melt processability and properties of metal neutralized sulfonated polymers by the use of a reactive plasticizer wherein the plasticizer improves the flow of the ionic polymer during processing, and subsequently is polymerized by a free radical process into a thermoset polymer. The resultant composition is an intimate blend of ionic polymer with a thermoset polymer, wherein the resultant composition has improved properties.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: March 20, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Henry S. Makowski, Jan Bock
  • Patent number: 4143185
    Abstract: A process is disclosed for fabricating a thermoplastic, which thermoplastic is either a thermoplastic ionomer or a multiphase graft or block copolymer of the ABA. (AB).sub.n, or ##STR1## wherein n is greater than 1 and wherein the polymer blocks, A and B, are each thermoplastic resins having softening points substantially above room temperature with the B block being present in at least about 30 wt. % of the total polymer. The thermoplastic composition is first suspended in finely divided form in a liquid medium in a sufficient amount such that the solids content of the resulting suspension is in the range of from about 15 to about 75 wt. %. The liquid medium must be nonvolatile and must be capable of plasticizing the B block (or the backbone if the ionomer is employed) of the thermoplastic composition above the softening point of that block but must not be capable of plasticizing the A block to a substantial extent. The suspension is then applied as a coating to any desired surface, e.g.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: March 6, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert D. Lundberg, Henry S. Makowski
  • Patent number: 4134870
    Abstract: This invention relates to elastomeric blend compositions of a neutralized sulfonated elastomeric polymer. The solid, gel-free compositions include a neutralized sulfonated elastomeric polymer, a hydroxyalkyl carboxylate ester, a non-polar wax, wherein the resultant compositions have both improved physical and rheological properties.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: January 16, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Charles P. O'Farrell
  • Patent number: 4131586
    Abstract: Polymers having one or more sulfonic acid groups covalently bonded to one or more carbon atoms including the polymer are stabilized against thermal and hydrolytic degradation by reaction with an oxirane. The solid, gel-free hydroxyalkyl sulfonates thus formed are readily converted to thermoplastic ionomers by reaction with a metallic base or salt of a weak acid. The polymeric hydroxy alkylsulfonates possess a low melt viscosity and thus are readily mixed with neutralizing agents, plasticizers or other polymers and thereafter converted to ionomers by reaction with the neutralizing agent which is a metallic base or salt of a weak acid. The formulated solid gel-free ionomers are thermoelastic in nature and can be extruded, injected molded, and compression molded to useful products.
    Type: Grant
    Filed: November 29, 1977
    Date of Patent: December 26, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Henry S. Makowski, Charles P. O'Farrell