Patents Represented by Attorney George L. Tone
  • Patent number: 4426492
    Abstract: Stable three dimensional hydrogels which absorb water, but are insoluble in water, and are particularly useful for the making of soft contact lenses, are prepared by reacting a water insoluble polyvinyl resin which contains reactive hydroxyl groups in its polymer chain, with a di- or poly-basic acid anhydride, to thereby introduce pendant carboxyl groups into the polymer chain, followed by treatment of the thus obtained carboxylated polymer to effect a limited amount of crosslinking thereof whereby a sparingly crosslinked hydrophilic polymer is obtained which when immersed in water absorbs water and swells to form a hydrogel, which does not dissolve in water.
    Type: Grant
    Filed: September 3, 1981
    Date of Patent: January 17, 1984
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4171457
    Abstract: 1-Hydroxy-2-Bromo-3-Allyloxypropane (allyl glycidyl ether bromohydrin) and 1-hydroxy-2-bromo-3-allyloxypropane phophoric acid ester (allyl glycidyl ether bromophosphate), which are useful as polymerizable flame-retardants, are described. 1-Hydroxy-2-bromo-3-allyloxypropane was prepared by the reaction of equimolar amounts of allyl glycidyl ether and hydrobromic acid, in acetic acid, preferably at a temperature in the range of 25.degree.-50.degree. C. and the thus obtained allyl glycidyl ether bromohydrin was phosphated by reaction with a substantially equimolar amount of polyphosphoric acid, preferably at a temperature in the range of about 40.degree.-50.degree. C., to produce the 1-hydroxy-2-bromo-3-allyloxypropane phosphoric acid ester.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: October 16, 1979
    Assignee: Alcolac Inc.
    Inventor: Seymour M. Linder
  • Patent number: 4163092
    Abstract: Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and crosslinking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a cationic monomer -- usually an ester of acrylic or methacrylic acid with an amino alcohol, the terminal amino group of which may be quaternized, such as dimethylaminoethyl methacrylate or acrylate and the quaternized derivatives thereof, and (c) a cross-linking agent, such as glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acrylic monomer such as an alkyl acrylate or methacrylate, acrylamides etc.
    Type: Grant
    Filed: August 18, 1977
    Date of Patent: July 31, 1979
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4144212
    Abstract: Air-curing copolymer latices are described. The preferred copolymer latices are prepared by emulsion copolymerization, in the presence of a free radical polymerization catalyst such as inorganic or organic peroxide polymerization catalysts, with a blend (in % by weight based on the total weight of all monomers used) of (a) about 1% to about 20% of dicyclopentadienyl acrylate or dicyclopentadienyl methacrylate, (b) about 99% to about 20% of an alkyl acrylate or methacrylate, including mixtures of such monomers, and preferably a lower alkyl acrylate or methacrylate in which the alkyl groups contain from 1 to 4 carbon atoms, (c) 0% to about 5% of acrylic acid or methacrylic acid, and (d) 0% to about 85% of other monoethylenically unsaturated copolymerizable monomers.
    Type: Grant
    Filed: March 6, 1978
    Date of Patent: March 13, 1979
    Assignee: Alcolac Inc.
    Inventors: Seymour M. Linder, John W. Calentine
  • Patent number: 4110286
    Abstract: Novel emulsifiable prepolymers for polyurethanes comprising an isocyanate prepolymer a minor proportion of the terminal isocyanate groups of which have been reacted with a quaternized tertiary amino alcohol, storage stable polyurethane latices produced therefrom and methods of making them are described. In a preferred embodiment a conventional isocyanate terminated prepolymer is first produced by the reaction of a polyol, preferably a diol of polyether or polyester origin, with a stoichiometric excess of a polyisocyanate, preferably a diisocyanate such as toluene diisocyanate; this prepolymer is then reacted, under anhydrous conditions, with a small amount, usually from about 1% to 5%, preferably about 1% to about 2%, by weight of a quaternized tertiary amino alcohol. Alternatively, a small amount of the quaternized tertiary amino alcohol may be included in the mixture of polyol and excess isocyanate used for making the prepolymer.
    Type: Grant
    Filed: February 7, 1977
    Date of Patent: August 29, 1978
    Assignee: Alcolac Inc.
    Inventors: Jan E. Vandegaer, John W. Calentine
  • Patent number: 4071508
    Abstract: Novel anionic hydrogels, containing acidic groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are stable three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and cross-linking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a polymerizable acidic monomer containing a sulfonic acid, sulfate or phosphate group in its molecular structure, such as sulfo-ethyl acrylate or methacrylate or a sulfate or phosphate derivative of a hydroxyalkyl- acrylate or methacrylate, and (c) a cross-linking agent, such as a glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acryloid monomer such as an alkyl acrylate or methacrylate, acrylamides etc.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: January 31, 1978
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4060678
    Abstract: Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and crosslinking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a cationic monomer -- usually an ester of acrylic or methacrylic acid with an amino alcohol, the terminal amino group of which may be quaternized, such as dimethylaminoethyl methacrylate or acrylate and the quaternized derivatives thereof, and (c) a cross-linking agent, such as a glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acrylic monomer such as an alkyl acrylate or methacrylate, acrylamides etc.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: November 29, 1977
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4058491
    Abstract: Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are stable, three-dimensional polymer networks, having good water permeability and mechanical properties.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: November 15, 1977
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4049608
    Abstract: Novel copolymerizable esters of cinnamic acid or an .omega.-alkenoic acid of from 4 to 18 carbon atoms, such as undecylenic acid, with certain hydroxyalkane sulfonic acids, such as isethionic acid, are described together with processes of making them and copolymers thereof. These novel copolymerizable esters may be made by reaction of the .omega.-alkenoic or cinnamic acid with the hydroxyalkane sulfonic acid or a sultone, such as propane sultone. These novel ester are useful as copolymerizable surfactants in the emulsion polymerization of ethylenically unsaturated monomers; particularly for the production of self-stabilizing latices of polymeric materials possessing excellent mechanical stability and from which can be deposited films having improved adhesion, pigment wetting and bonding properties and greatly improved resistance to water.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: September 20, 1977
    Assignee: Alcolac Inc.
    Inventors: Robert Steckler, Fred Robinson, Robert F. Farmer, III
  • Patent number: 4036788
    Abstract: Novel anionic hydrogels, containing acidic groups, and their preparation are described. These novel hydrogels are stable, three-dimensional polymer networks, having good water permeability and mechanical properties.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: July 19, 1977
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4029578
    Abstract: An improved catalytic process for the ozonation of water containing organic contaminants is disclosed. In this process the water, which may be either waste water or potable water, containing organic contaminants is contacted with ozone, preferably at a pH in the range of about 6.8 to about 7.8 (controlled by buffering if necessary), in the presence of a mixed heterogeneous catalyst comprising water insoluble salts, preferably an insoluble carbonate, sulfate, oxide, halide or sulfide, of at least two metals selected from the group consisting of copper, cadmium and the group VIII metals, preferably iron, cobalt or nickel although other group VIII metals such as platinum or Palladium may be used if desired.
    Type: Grant
    Filed: September 4, 1975
    Date of Patent: June 14, 1977
    Assignee: Environmental Research and Applications, Inc.
    Inventor: Amos Turk
  • Patent number: 4022851
    Abstract: 1-Hydroxy-2-Bromo-3-Allyloxypropane (allyl glycidyl ether bromohydrin) and 1-hydroxy-2-bromo-3-allyloxypropane phosphoric acid ester (allyl glycidyl ether bromophosphate), which are useful as polymerizable flame-retardants, are described. 1-Hydroxy-2-bromo-3-allyloxypropane was prepared by the reaction of equimolar amounts of allyl glycidyl ether and hydrobromic acid, in acetic acid, preferably at a temperature in the range of 25.degree.-50.degree. C. and the thus obtained allyl glycidyl ether bromohydrin was phosphated by reaction with a substantially equimolar amount of polyphosphoric acid, preferably at a temperature in the range of about 40.degree.-50.degree. C., to produce the 1-hydroxy-2-bromo-3-allyloxypropane phosphoric acid ester.
    Type: Grant
    Filed: July 28, 1976
    Date of Patent: May 10, 1977
    Assignee: Alcolac Inc.
    Inventor: Seymour M. Linder
  • Patent number: 4009201
    Abstract: Novel polymerizable cationic monomers, which contain two or more cationic groups in the molecule, and homopolymers and copolymers thereof are described. These novel cationic monomers are compounds represented by the general formula: ##STR1## AND THE QUATERNIZED DERIVATIVES THEREOF (IN WHICH THE TERMINAL TERTIARY AMINO GROUP HAS BEEN QUATERNIZED TO A QUATERNARY AMMONIUM GROUP) OF THE FORMULA: ##STR2## In the forgoing Formulas 1 and 2: A, each of which may be the same or different, represents an alkylene group of from 1 to about 20 carbon atoms but including oxygen interrupted alkylene groups (i.e.; a polyglycol ether group of the formula ##STR3## WHEREIN R.sup.5 represents H, methyl or ethyl and x represents an integer of from 1 to about 20);R represents H or methyl;R.sup.1 represents H or, when R is H, an alkyl group of 1 to 4 carbon atoms, R.sup.1 preferably H or methyl;R.sup.2, r.sup.3 and R.sup.
    Type: Grant
    Filed: May 20, 1974
    Date of Patent: February 22, 1977
    Assignee: Alcolac Inc.
    Inventors: Robert Steckler, Seymour Martin Linder