With Ethylenically Unsaturated Reactant Patents (Class 528/376)
  • Patent number: 4749756
    Abstract: A modified Williamson etherification in the presence of phase transfer catalyst is used to synthesize alternating block copolymers and regular copolymers. Unsaturated polyethers of a polynuclear dihydric phenol containing chloroallylic (electrophilic) end groups (prepared from cis- or trans-1,4-dichloro-2-butene and Bisphenol A) and aromatic poly(ether sulfone)s containing terminal phenol (nucleophilic) groups are polycondensed in the presence of tetrabutylammonium hydrogen sulfate as phase transfer catalyst to give alternating block copolymers. The same telechelic polymers were chain-extended with dinucleophilic or dielectrophilic monomers under similar reaction conditions. Both the regular copolymers and the alternating block copolymers were characterized by gel permeation chromatography and DSC.
    Type: Grant
    Filed: January 16, 1987
    Date of Patent: June 7, 1988
    Assignee: The B. F. Goodrich Company
    Inventor: Virgil Percec
  • Patent number: 4728712
    Abstract: A method for producing mercaptan terminated liquid polymers with increased chemical reactivity and reduced odor is disclosed which involves heating the polymeric liquid material under conditions which avoid oxidation and depolymerization of the material while removing at least 50 weight percent of low molecular weight mercaptan compounds to produce a stripped polymer material having an increased cure rate and reduced obnoxious mercaptan odor.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: March 1, 1988
    Assignee: Products Research & Chemical Corp.
    Inventors: Hakam Singh, Jack W. Hutt
  • Patent number: 4701514
    Abstract: Oligomers of polyarylene polyethethers (PAPE) having a mol wt Mn in the range from 1000 to about 10,000 are converted to difunctionalized oligomers so as, in the first instance, to provide a reactive double bond (for example, a vinylbenzyl group) at each end of the PAPE; and, in the second instance, to provide a triple bond (benzylethynyl group) at each end of the PAPE. The PAPE most preferably has a repeating unit which is the residuum of two dihydric phenols or thiophenols ("DHP") linked through a C=O, --S--S--, or --SO.sub.2 -group, or a Si or C atom, and or ether O, or thioether S atoms. The preferred repeating unit is formed by reaction of a DHP such as bisphenol A (BPA) with a halogenated DHP such as dichlorophenyl sulfone (DCPS) so as to provide an alternating configuration. The repeating unit may also include a linking residue of a reactive solvent which residue provides chain extension in the backbone.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: October 20, 1987
    Assignee: B.F. Goodrich Company
    Inventor: Virgil Percec
  • Patent number: 4623703
    Abstract: A two-step method is disclosed for chemically synthesizing substituted butadiene polymers from 1,4-disubstituted butynes. The first step in the synthesis of the butadiene polymer is the polymerization of 1,4-disubstituted butyne monomers. The substituted butyne polymer which results is then isomerized to the corresponding substituted butadiene polymer by subjecting the butyne to a weak organic base such as triethylamine. The isomerization reaction can be performed under very mild conditions and proceeds at ambient temperature.
    Type: Grant
    Filed: October 24, 1984
    Date of Patent: November 18, 1986
    Assignee: The University of Texas System
    Inventor: Budalur S. Thyagarajan
  • Patent number: 4587329
    Abstract: Dense star polymers having terminal group densities greater than conventional extended star polymers exhibit greater and more uniform reactivity than their corresponding conventional star polymers. For example, a third generation, hydroxy-terminated polyether dense star polymer can be prepared from pentaerythrityltetrabromide and 4-hydroxymethyl-2,6,7-trioxabicyclo[2.2.2]-octane which has a molecular volume less than 80 percent of the volume of a conventional extended star polymer made from similar materials. Such dense star polymers are useful as demulsifiers for oil/water emulsions, wet strength agents in the manufacture of paper, proton scavengers, calibration standards for electron microscopy, and agents for modifying viscosity in aqueous formulations such as paints.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: May 6, 1986
    Assignee: The Dow Chemical Company
    Inventors: Donald A. Tomalia, James R. Dewald
  • Patent number: 4574139
    Abstract: A polymer having a fluorine-containing end group which is produced by polymerizing a monomer capable of radical polymerization in the presence of a fluorine-containing thiol; a vinyl ester polymer having a fluorine-containing end group which is produced by polymerizing vinyl ester in the presence of a fluorine-containing thiol; and vinyl alcohol polymer having a fluorine-containing end group which is produced by saponifying the said vinyl ester polymer; and processes for producing the same are provided.The polymers of this invention are superior in water repellency, oil repellency, heat resistance, chemical resistance, and surface activity which are characteristic of fluorocarbon compounds, and are expected to find use in various application areas.
    Type: Grant
    Filed: May 25, 1984
    Date of Patent: March 4, 1986
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshiaki Sato, Junnosuke Yamauchi, Takuji Okaya
  • Patent number: 4562243
    Abstract: Oligomers of polyarylene polyethers (PAPE) having a mol wt Mn in the range from 1000 to about 10,000 are converted to difunctionalized oligomers so as, in the first instance, to provide a reactive double bond (for example, a vinylbenzyl group) at each end of the PAPE; and, in the second instance, to provide a triple bond (benzylethynyl group) at each end of the PAPE. The PAPE most preferably has a repeating unit which is the residuum of two dihydric phenols or thiophenols ("DHP") linked through a C.dbd.O, --S--S--, or --SO.sub.2 -group, or a Si or C atom, and or ether O, or thioether S atoms. The preferred repeating unit is formed by reaction of a DHP such as bisphenol A (BPA) with a halogenated DHP such as dichlorophenyl sulfone (DCPS) so as to provide an alternating configuration. The repeating unit may also include a linking residue of a reactive solvent which residue provides chain extension in the backbone.
    Type: Grant
    Filed: March 6, 1984
    Date of Patent: December 31, 1985
    Assignee: The B. F. Goodrich Company
    Inventor: Virgil Percec
  • Patent number: 4560457
    Abstract: Adhesives adapted especially for bonding optical elements and consisting of, as major components, a polyfunctional acrylate and a polythiol, a radical generating photoinitiator, a radical generating heatactivated-curing initiator and a stabilizer against premature onset of curing.
    Type: Grant
    Filed: December 11, 1981
    Date of Patent: December 24, 1985
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Kazufumi Ogawa
  • Patent number: 4463169
    Abstract: Polymerizable compositions comprise(a) a compound containing(i) at least one acryloyloxy or methacryloyloxy group,(ii) at least one allyl, methallyl, or 1-propenyl group attached, either directly, or through an oxygen atom or an oxycarbonyl group, to a carbon atom which forms part of an aromatic or cycloaliphatic nucleus,(b) a compound containing in the molecule both(iii) at least one acryloyloxy or methacryloyloxy group and(iv) at least one --COOH group, and(c) a compound containing at least two mercaptan groups directly attached to aliphatic carbon atoms.Examples of (a) are 2,2-bis(3-allyl-4-(3-(methacryloyloxy)-2-(2-carboxyethylcarbonyloxy)propox y)phenyl)propane, 1-(allyloxycarbonyl)-2,4-bis(3-(methacryloyloxy)-2-(2-carboxyethylcarbonyl oxy)propoxycarbonyl)benzene, and diallyl bis(3-methacryloyloxy)-2-(2-carboxyethylcarbonyloxy)propyl) esters of benzophenone-3,4,3',4'-tetracarboxylic acid. Examples of (b) are acrylic acid and 2-(methacryloyloxy)ethyl 5-carboxycyclohex-1-ene-4-carboxylate.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: July 31, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4435497
    Abstract: Polymerizable compositions comprise(a) a compound containing(i) at least one acryloyloxy or methacryloyloxy group,(ii) at least one allyl, methallyl, or 1-propenyl group attached, either directly or through an oxygen atom or an oxycarbonyl group, to a carbon atom which forms part of an aromatic or cycloaliphatic nucleus, and(iii) at least one carboxylic acid group,(b) a compound containing at least two mercaptan groups directly attached to aliphatic carbon atoms, in a proportion as to supply at least 0.8 such --SH group per allyl, methallyl, and 1-propenyl group in (a) but less than 1.0 such --SH group in (a) per acryloyl, methacryloyl, allyl, methallyl, and 1-propenyl group.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: March 6, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4266080
    Abstract: Perfluoroalkyl compounds containing ether groups have the formulaR.sub.f R.sub.1 SCH.sub.2 CH.sub.2 O T Zwherein R.sub.f is a perfluoroalkyl, R.sub.1 is alkylene or alkyleneoxy or aminoalkylene, T is alkylene, and Z is hydrogen; hydroxy; NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 each is alkyl or together with nitrogen form a heterocyclic ring; N.sup.+ R.sub.3 R.sub.4 (R.sub.5)X.sub.z.sup.-y, where R.sub.5 is hydrogen, oxide, alkyl, or substituted alkyl, X is an anion, and y is 1 or 2; z is 0 or 1 or is --OCH.sub.2 CH.sub.2 SR.sub.1 R.sub.f ; can be prepared directly by free-radical catalyzed addition of a perfluoroalkylthiol to a vinyl ether or subsequent reaction. These compounds are useful as surfactants and oil spill collecting agents.
    Type: Grant
    Filed: February 2, 1978
    Date of Patent: May 5, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Karl F. Mueller
  • Patent number: 4255539
    Abstract: Sulfur-modified polychloroprene in alkaline aqueous emulsion is prepared by incorporating one or more organic polysulfides which act as peptizing agents during the polymerization of the chloroprene. The sulfur-modified polychloroprenes obtained have stable viscosities.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: March 10, 1981
    Assignee: Distugil
    Inventors: Paul Branlard, Jean-Pierre Merle
  • Patent number: 4220513
    Abstract: Polymerizable compositions comprise(a) a compound containing in the same molecule both at least one 1,2-epoxide group and at least two groups chosen from allyl, methallyl, and 1-propenyl groups, e.g., 2,2-bis(3-allyl-4-(glycidyloxy)phenyl)propane or bis(3-(1-propenyl)-4-(glycidyloxy)phenyl)methane, and(b) a compound containing at least two mercaptan groups per molecule, e.g., pentaerythritol tetrathioglycollate.The compositions are caused to polymerize by the action of irradiation or free-radical catalysts. They may, if desired, also contain a heat-curing crosslinking agent for epoxide resins; the epoxide-containing polymers so obtained can be subsequently crosslinked in situ. The compositions are useful in various two-stage operations, such as the production of multilayer printed circuits.
    Type: Grant
    Filed: January 19, 1979
    Date of Patent: September 2, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Abdul-Cader Zahir
  • Patent number: 4218559
    Abstract: The present invention relates in general to vulcanizable elastomers of thiodiethanol and, in particular, to the provision of a novel vulcanization system for vulcanizable elastomers of thiodiethanol, comprising sulfur and certain pyrazine compounds.
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: August 19, 1980
    Assignee: American Cyanamid Company
    Inventors: Donald R. Maulding, Rudolf A. Behrens
  • Patent number: 4202963
    Abstract: The present invention relates in general to sulfur-vulcanizable elastomers derived from thiodiethanol and, in particular to the provision of a novel vulcanization system therefor comprising sulfur and an aliphatic linear, branched chain of cyclic polyethyleneamine or a dissociable organic salt thereof.
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Rudolf A. Behrens
  • Patent number: 4197382
    Abstract: A rubber composition for use as a cover of rubber pipes or hoses, comprising a terpolymer rubber composed of 35 to 80 mole% of epichlorohydrin, 15 to 50 mole% of ethylene oxide and 5 to 15 mole% of an unsaturated epoxide, and a di- or tri-mercapto-s-triazine as a vulcanization agent.
    Type: Grant
    Filed: January 3, 1979
    Date of Patent: April 8, 1980
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Hiroshi Fukushima, Akio Maeda, Masaaki Inagami, Kinro Hashimoto
  • Patent number: 4182848
    Abstract: Novel photocurable compositions employing the addition of thiols to polymers having terminal vinyl-acetal functions, products prepared therefrom, and process for preparation thereof are disclosed. The cured products are films useful in coating floor tile, fabrics, and wooden articles.
    Type: Grant
    Filed: September 20, 1978
    Date of Patent: January 8, 1980
    Assignee: Thiokol Corporation
    Inventors: Claude J. Schmidle, Robert Barclay, Jr.
  • Patent number: 4163832
    Abstract: Episulfides are reacted with mono, di or trithiols in the presence of tertiary aliphatic amines or tertiary aliphatic phosphines, to form corresponding thioether thiols by a highly selective anionic mechanism. Increasing episulfide-thiol ratios result in polythioether thiols of increasing molecular weights. Using two or more episulfides, block copolymers can be prepared. The reactive terminal thiol functionality and the segmented crystalline and amorphous block structure of the new polymers makes them particularly useful for castable rubber applications.
    Type: Grant
    Filed: November 21, 1977
    Date of Patent: August 7, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventor: Alexis A. Oswald
  • Patent number: 4157421
    Abstract: Novel photocurable compositions employing the addition of thiols to polymers having terminal vinyl-acetal functions, products prepared therefrom, and process for preparation thereof are disclosed. The cured products are films useful in coating floor tile, fabrics, and wooden articles.
    Type: Grant
    Filed: September 7, 1976
    Date of Patent: June 5, 1979
    Assignee: Thiokol Corporation
    Inventors: Claude J. Schmidle, Robert Barclay, Jr.
  • Patent number: 4117017
    Abstract: This invention relates to a process for preparing thiols and polythiols by the addition of a thiolcarboxylic acid, e.g., thiolacetic acid, to ethylenically unsaturated compounds in the presence of an initiator comprising a pinacol of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy to obtain a thiol ester which is thereafter hydrolyzed to yield the corresponding thiol.
    Type: Grant
    Filed: April 18, 1977
    Date of Patent: September 26, 1978
    Assignee: W. R. Grace & Co.
    Inventors: Charles Robert Morgan, Richard Wayne Bush
  • Patent number: 4104283
    Abstract: New compounds of the structure ##STR1## WHERE R is an aromatic, alicyclic or aliphatic group of at least 2 C atoms and up to 18 C atoms, x is an integer from 1 to 9, R' is H, a lower alkyl grup of 1-4 C atoms or --CH.sub.2 Cl, y is an integer of from 0-10 and z is an integer of from 2 to 6 are prepared by reacting a polythioetherpolythiol with an olefinically unsaturated epoxide or by dehydrohalogenating the corresponding halohydrins. The new compounds are useful as diluents for epoxy resins to reduce their viscosity and to improve flexibility of the cured resins.
    Type: Grant
    Filed: November 26, 1971
    Date of Patent: August 1, 1978
    Assignee: The Dow Chemical Company
    Inventor: Richard A. Hickner