Material Is A Nitrogen-containing Compound Other Than A Lactam Patents (Class 528/315)
  • Patent number: 4595730
    Abstract: Unsaturated polyamide polymers are provided which are comprised of a polyamide chain terminated at one end by a group containing at least one double bond. The polymers are particularly useful in the preparation of molded object coatings, water tight joints, grafting onto thermoplastic polymers or copolymers, and the like.
    Type: Grant
    Filed: October 31, 1984
    Date of Patent: June 17, 1986
    Assignee: Atochem
    Inventors: Philippe Blondel, Camille Jungblut
  • Patent number: 4595746
    Abstract: A process for polymerizing .epsilon.-caprolactam to form a nylon-6 polymer in which a reactant stream containing .epsilon.-caprolactam and a lactam polymerization initiator is brought into polymerizing admixture with a reactant stream containing .epsilon.-caprolactam and a lactam magnesium halide, wherein sufficient 2-oxo-1-pyrrolidinyl compound is added to the admixture either as 2-pyrrolidinone, 2-oxo-pyrrolidinyl magnesium halide or 2-oxo-1-pyrrolidinyl capped initiator compound to enhance the rate of polymerization of the .epsilon.-caprolactam.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: June 17, 1986
    Assignee: Monsanto Company
    Inventors: James D. Gabbert, Ross M. Hedrick
  • Patent number: 4594409
    Abstract: A sequential polyamino acid resin having a remarkably high molecular weight and special amino acid sequence as repeating unit in the resin can be produced by conducting polycondensation of a peptide active ester acid salt in an aprotic polar solvent in the presence of a tertiary amine and phosphorus pentoxide.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: June 10, 1986
    Assignee: Nitto Boseki Co., Ltd.
    Inventors: Ikuo Hayashi, Tadao Itikawa, Kiyoshi Shimizu
  • Patent number: 4574054
    Abstract: The invention is concerned with a combination of molecular weight controllers to be used in the production of a stabilized polyamide having a low content of monomers and oligomers and a high dye-taking capability by polymerization of caprolactam. The combination comprises: (a) a primary monofunctional amine having its boiling point at 180.degree. C. above, and a basic dissociation constant K.sub.b .gtoreq.1.7.times.10.sup.-5 ; (b) a monofunctional organic acid having a K.sub.a >1.5.times.10.sup.-5 ; and (c) an aminoacid containing at least ten carbon atoms having the --NH.sub.2 group salified by a monofunctional organic or inorganic acid which has K.sub.a >1.0.times.10.sup.-2. With this combination, a polyamide is obtained which, following residence in the molten state, has a monomer content of 0.25% or less and a dimer content of 0.15% or less.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: March 4, 1986
    Assignee: Snia Fibre S.p.A.
    Inventors: Aldemaro Ciaperoni, Alberto Cappelli
  • Patent number: 4543407
    Abstract: Nylon-type polyamides are produced from a diamine and a diamide in contact with an oxygenated phosphorus compound catalyst. For example, high quality nylon-6,6 is manufactured by contacting hexamethylenediamine and adipamide in water with an oxygenated phosphorus compound at an elevated temperature and pressure.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: September 24, 1985
    Assignee: The Standard Oil Company
    Inventors: Benedict S. Curatolo, Robert C. Sentman, Gerald P. Coffey
  • Patent number: 4525576
    Abstract: A sequential polyamino acid resin having a remarkably high molecular weight and special amino acid sequence as repeating unit in the resin can be produced by conducting polycondensation of a dipeptide active ester acid salt in an aprotic polar solvent in the presence of a tertiary amine and phosphorus pentoxide.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: June 25, 1985
    Assignee: Nitto Boseki Co. Ltd.
    Inventors: Ikuo Hayashi, Tadao Itikawa, Keizo Ogihara, Kiyoshi Shimizu
  • Patent number: 4518765
    Abstract: An improved process for the anionic polymerization of lactams is described. Particular azetidinedione compounds are employed as promoters and their use not only permits low polymerization temperatures but gives rise to faster polymerization reactions than prior art procedures allow.The rapid polymerization of caprolactam in accordance with the present invention makes the process particularly suited to RIM procedures for preparing molded polyamides.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: May 21, 1985
    Assignee: The Upjohn Company
    Inventors: Steven J. Grossman, Kemal Onder
  • Patent number: 4511709
    Abstract: High molecular weight block copolyamides useful in the production of fibers of high strength and modulus, having the following formula: ##STR1## wherein X is --CH.sub.2 --.sub.m, wherein m is 0 to 12, ##STR2## wherein Z is C(CH.sub.3).sub.2, zero, oxygen or SO.sub.2, are prepared from N,N'-bis(4-aminophenyl) terephthalamide having the formula: ##STR3## which is itself prepared by condensing aniline with dimethyl terephthalate or terephthalic acid, nitrating the product produced thereby and finally hydrogenating the resultant compound.
    Type: Grant
    Filed: February 15, 1983
    Date of Patent: April 16, 1985
    Assignee: Korea Advanced Institute of Science and Technology
    Inventors: Hans S. Yoon, Wha S. Lee
  • Patent number: 4507465
    Abstract: A block copolyamide having effectively improved impact strength is obtained by polymerizing a mixture comprising substantially from about 50 to about 95 parts by weight of lactam and from about 50 to about 5 parts by weight of polyol in the presence of catalyst for an anionic polymerization and activator represented by the following formula (I); ##STR1## wherein A denotes a bifunctional organic residue having at least one kind of heteroatoms selected from the group consisting of N, O, S, F, Cl, Br and I, and Y and Y' denote an acyl group selected from the group consisting of ##STR2## respectively, and n and n' denote an integer of 3 to 11 respectively, or by polymerizing, in the presence of catalyst for anionic polymerization, a mixture comprising substantially from about 50 to about 95 parts by weight of lactam and from about 5 to about 50 parts by weight of prepolymer obtained by a reaction of polyol and activator represented by the above formula (I), wherein A denotes a bifunctional aromatic residue having
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: March 26, 1985
    Assignee: Toray Industries, Inc.
    Inventors: Kazumasa Chiba, Kazuhiko Kobayashi, Tosaku Susuki
  • Patent number: 4497948
    Abstract: Polyimide resins suitable for use as composite matrix materials are formed by copolymerization of maleic and norbornenyl endcapped monomers and oligomers. The copolymers can be cured at temperatures under about 300.degree. C. by controlling the available concentration of the maleic end-capped reactant. This control can be achieved by adding sufficient amounts of said maleic reactant, or by chemical modification of either copolymer, so as to either increase Diels-Alder retrogression of the norbornenyl capped reactant and/or holding initiation and polymerization to a rate compatible with the availability of the maleic-capped reactant.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: February 5, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Richard W. Lauver
  • Patent number: 4496514
    Abstract: This invention relates to reaction injection molding of a mixture of lactams in presence of a catalyst and a promotor which is carried out by mixing at least two lactams in a liquid state with the catalyst and promoter before injecting the mixture into a preheated mold. The use of a mixture of lactams results in a supercooled mixture which remains liquid at ambient temperature for at least 2 hours.
    Type: Grant
    Filed: January 27, 1983
    Date of Patent: January 29, 1985
    Assignee: The B. F. Goodrich Company
    Inventors: Wei-Yeih W. Yang, Yoshihisa Okamoto
  • Patent number: 4490520
    Abstract: A process for preparing polyamides having improved impact strength and elongation comprising polymerizing an -lactam in the presence of (1) an alkali catalyst and (2) the reaction product of (a) a polyfunctional co-catalyst such as a polyisocyanate and (b) a polyoxyalkalene amine. The polyamides of the present invention are particularly useful for making strong tough molded or cast articles.
    Type: Grant
    Filed: February 24, 1983
    Date of Patent: December 25, 1984
    Assignee: UBE Industries, Ltd.
    Inventors: Masao Ogasa, Masao Nishiyama, Kaoru Ohtsuki
  • Patent number: 4461885
    Abstract: Polyamides can be formed in good yields by the copolymerization of at least one alpha, beta-unsaturated nitrile with at least one amino acid. These polymers are suitable for use as fibers, plastics, films and molding resins.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: July 24, 1984
    Assignee: The Standard Oil Company
    Inventors: Mu-Yen M. Wu, Lawrence E. Ball
  • Patent number: 4448956
    Abstract: Polyamides such as nylon-6 type polyamides are prepared by the reaction or copolymerization of a major amount by weight of a lactam and a minor amount by weight of a graft copolymer of maleic anhydride on a low molecular weight liquid conjugated diene polymer or copolymer or of a copolymer of a conjugated diene and a monovinyl aryl monomer or a nitrile. For example, a graft of maleic anhydride on liquid butadiene/acrylonitrile copolymer is copolymerized with epsilon-caprolactam using an anionic lactam polymerization catalyst (a lactamate salt) like the reaction product of ethyl magnesium bromide and epsilon-caprolactam. The present invention may be useful in a RIM (Reaction Injection Molding) process. The resulting polyamides have improved impact strength and water resistance. They can be used to make automobile and truck bodies and parts.
    Type: Grant
    Filed: May 10, 1983
    Date of Patent: May 15, 1984
    Assignee: The General Tire & Rubber Company
    Inventors: Gerd M. Lenke, Earl G. Melby, Hubert J. Fabris
  • Patent number: 4448955
    Abstract: This invention provides a single stage melt polymerization process for the production of an improved type of high molecular weight polybenzimidazole, which involves the use of a tin-containing polymerization catalyst.The process provides poly-2,2'-(m-phenylene)-5,5'-bibenzimidazole of improved color and Plugging Value, and is further characterized by an Inherent Viscosity of at least about 0.5 dl/g, and a weight average molecular weight of at least about 100,000.
    Type: Grant
    Filed: April 7, 1983
    Date of Patent: May 15, 1984
    Assignee: Celanese Corporation
    Inventors: Eui W. Choe, Anthony B. Conciatori
  • Patent number: 4436897
    Abstract: An improved process for the preparation of fiber-forming polycaprolactam by polymerizing .epsilon.-caprolactam, and an aqueous extract containing .epsilon.-caprolactam and caprolactam oligomers, which extract has been obtained by extracting polycaprolactam with water, wherein the aqueous extract contains from 0.1 to 5.0% by weight of oligomers of caprolactam, based on the monomeric caprolactam in the aqueous extract.
    Type: Grant
    Filed: August 24, 1982
    Date of Patent: March 13, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Hugo Strehler, Werner Hoerauf, Friedrich Urbanek
  • Patent number: 4435547
    Abstract: Poly-2-pyrrolidone polymer and compositions having improved thermal stability via the capping of at least a portion of the amino and/or carboxy end group of the polymer and processes for preparing such polymers and compositions. The processes are characterized by the reaction of the polymer with alkanolamines and/or alkyl polyamines. The products afford improved melt processability.
    Type: Grant
    Filed: February 9, 1983
    Date of Patent: March 6, 1984
    Assignee: Chevron Research Company
    Inventors: Gar L. Woo, Phillip H. Parker
  • Patent number: 4412061
    Abstract: This invention relates to a new process for preparing a copolyamide comprising polymerizing an alpha, beta-unsaturated nitrile and water with a molar excess of a lactam. In one embodiment, acrylonitrile, water and caprolactam are polymerized to form a nylon-3,6.
    Type: Grant
    Filed: December 24, 1980
    Date of Patent: October 25, 1983
    Assignee: The Standard Oil Company
    Inventors: Mu-Yen M. Wu, Lawrence E. Ball
  • Patent number: 4405777
    Abstract: This invention relates to a new process for preparing a copolyamide comprising polymerizing an alpha, beta-unsaturated nitrile and water with a molar excess of a lactam. In one embodiment, acrylonitrile, water and caprolactam are polymerized to form a nylon-3,6.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: September 20, 1983
    Assignee: Standard Oil Company
    Inventors: Mu-Yen M. Wu, Lawrence E. Ball
  • Patent number: 4389521
    Abstract: An aromatic and/or heterocyclic polyamide-amide type polar solvent composition is prepared by prepolymerizing an aromatic or heterocyclic diamine with an aromatic or heterocyclic or heterocyclic dicarboxylic acid chloride in a smaller molar equivalent than that of the diamine to prepare a prepolymer solution having a solution viscosity of 20 poise or less; by removing a by-product, hydrochloric acid, from the resultant prepolymer solution by neutralizing it with ammonia to such an extent that the pH of a mixture of 10 g of the neutralized mixture with 200 ml of water becomes 3.7 to 8.0; by high polymerizing the prepolymer with an additional amount of aromatic or heterocyclic dicarboxylic acid chloride, and; finally, by converting the entire amount of hydrochloric acid and 10 to 70% NH.sub.
    Type: Grant
    Filed: November 19, 1981
    Date of Patent: June 21, 1983
    Assignee: Teijin Limited
    Inventors: Keizo Shimada, Hiroshi Mera, Tsutomu Nakamura, Akihiro Aoki
  • Patent number: 4383065
    Abstract: Poly-2-pyrrolidone polymer compositions having improved melt processability via the capping of at least a portion of the amino and/or carboxy end group of the polymer and the incorporation therewith of certain epoxide organic isocyanate and/or polyol additive compositions. The melt extrusion of such compositions is also disclosed.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: May 10, 1983
    Assignee: Chevron Research Company
    Inventors: Gar L. Woo, Phillip H. Parker
  • Patent number: 4370467
    Abstract: A curable resin composition comprising (i) a catalytic composite comprising a peroxide and other catalytic component and (ii) a mixture or a preliminary reaction product of (a) a polyfunctional cyanate ester, prepolymer of the cyanate ester or coprepolymer of the cyanate ester and an amine and (b) a polyfunctional maleimide, prepolymer of the maleimide or coprepolymer of the maleimide and an amine and optionally (c) other component is disclosed. The composition cures rapidly at a low temperature and is preferable from view point of quantity production and workability. The composition is excellent in respect of adhering property, heat-resistance, moisture-resistance and chemical-resistance, and is useful for preparing laminated products, molded products, paint, powder paint, adhesive or varnish.
    Type: Grant
    Filed: July 3, 1980
    Date of Patent: January 25, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi
  • Patent number: 4366306
    Abstract: .epsilon.-Caprolactam is melt polymerized in the presence of water and from about 0.01 mole percent to less than about 0.6 mole percent of an amine boiling at a temperature greater than 245.degree. C. An amine may be a primary or secondary amine wherein the NH has attached thereto, for example alkyl radicals, cycloalkyl radicals, and the like. The resultant polymer has a methanol extractable content of 3 weight percent or less.
    Type: Grant
    Filed: October 29, 1980
    Date of Patent: December 28, 1982
    Assignee: The Dow Chemical Company
    Inventor: Harry A. Smith
  • Patent number: 4362862
    Abstract: A new type of poly-2-pyrrolidone suitable for melt spinning and a process for its preparation. The new poly-2-pyrrolidone is characterized in that the polymer in the virgin state has a relative viscosity (1 gram of polymer in 100 ml of 96% sulphuric acid at 20.degree. C.) of between 2.2 and 7.0, shows a weight loss of less than 5% by weight when heated from 20.degree. C. to the onset temperature of thermal degradation at a rate 4.degree. C. per minute, the ratio between the relative viscosities after and before melt spinning ranges between 0.50:1 and 0.95:1, and the relative viscosity after melt spinning is at least 1.90. The new poly-2-pyrrolidone is prepared by polymerization of 2-pyrrolidone in the presence of an anionic catalyst and an accelerator wherein N-(2-caprolactim)-caprolactam is used as the accelerator in an amount of between 0.05 and 5.0 mole percent relative to the monomer, and the polymerization is carried out at a temperature of between about 25.degree. and 70.degree. C.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: December 7, 1982
    Assignee: Stamicarbon, B.V.
    Inventors: Edmond H. J. P. Bour, Jean M. M. Warnier, Johannes A. L. Brouwers
  • Patent number: 4343933
    Abstract: Process which accelerates the activated and non-activated polymerization of 2-pyrrolidone. A prepared polymerization charge containing monomer and components of the initiation system is first allowed to polymerize at a temperature above the monomer melting temperature, then is cooled below the melting point of the mixture, and then the crystalline reaction mixture is heated to a polymerization temperature of 25.degree. to 60.degree. C.
    Type: Grant
    Filed: September 26, 1980
    Date of Patent: August 10, 1982
    Assignee: Vysoka skola chemicko-technologicka
    Inventors: Jan Roda, Jaroslav Kralicek
  • Patent number: 4316001
    Abstract: An initiator for the anionic polymerization of heterocyclic monomers comprises the product from the association of an alkali metal amide and the salt from at least one hydroxylated compound with the same alkali metal in an aprotic solvent. The hydroxylated compound is a primary alcohol, a secondary or tertiary alcohol, an ether alcohol, an amino alcohol, a polyether alcohol, a polyamino alcohol, a polyaminoetheralcohol, or an enol from a ketone.
    Type: Grant
    Filed: July 27, 1979
    Date of Patent: February 16, 1982
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Sylvie L. Boileau, Serge L. Lecolier, Serge F. Raynal
  • Patent number: 4303778
    Abstract: A method is described for the anionic polymerization and copolymerization of .omega.-aminoacid lactams. This end is attained at elevated temperatures in the presence of a polymerization initiator of the formulaMeZX.sub.m L.sub.nwherein Me is an alkali metal, Z is boron or aluminum, X is an alkoxy group and L is an organic residue derived from a lactam and being of the formula ##STR1## wherein a is an integer in the range 3-11, m is an integer in the range of 0-3, (m+n) is 4 and n is (4-m).
    Type: Grant
    Filed: January 17, 1978
    Date of Patent: December 1, 1981
    Assignee: Vysoka skola chemicko-technologicka
    Inventors: Jaroslav Kralicek, Vladimir Kubanek, Jiri Marik, Jaroslava Kondelikova, Jiri Machacek, Bohuslav Casensky
  • Patent number: 4292372
    Abstract: Polyvinylbutyral sheeting, plasticized with a hydrolyzable ester, having low acid concentration through the use of formic acid salt as an adhesion control agent.
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: September 29, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert E. Moynihan
  • Patent number: 4269966
    Abstract: Novel polyimide prepolymers are produced by reacting an unsaturated dicarboxylic acid imido acylchloride with a difunctional amine to produce the corresponding acid amide. Condensation of said reactants is preferably effected in solution in a low boiling solvent. The resulting prepolymer is hardened and completely polymerized by heating, preferably between about 80.degree. C. and about 400.degree. C., to yield a cross-linked, substantially infusible and insoluble polyimide resin and articles made therefrom.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: May 26, 1981
    Assignee: Technochemie GmbH Verfahrenstechnik
    Inventor: Horst Stenzenberger
  • Patent number: 4268660
    Abstract: A novel method of utilizing quaternary ammonium compounds to accelerate the polymerization of 2-pyrrolidone is disclosed. The method consists of dehydrating the hygroscopic quaternary ammonium compound by adding it to 2-pyrrolidone and distilling over, under vacuum, a portion of the pyrrolidone whereby the water is removed and then adding the residue to a conventional anhydrous polymerization mixture composed of an alkali metal salt of 2-pyrrolidone dissolved in 2-pyrrolidone and effecting polymerization by adding a polymerization initiator and heating the mixture to a temperature ranging from about room temperature to about 60.degree. C.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: May 19, 1981
    Inventors: Carl E. Barnes, Arthur C. Barnes
  • Patent number: 4247683
    Abstract: A method of recovering and recycling quaternary ammonium accelerators for the polymerization of 2-pyrrolidone is disclosed. The method consists of removing the quaternary ammonium compound together with unpolymerized 2-pyrrolidone by washing the polymer with a solvent for both, such as water or methanol, neutralizing the solution immediately after washing and then removing the solvent at a sufficiently low temperature so that the quaternary ammonium compound is not decomposed.
    Type: Grant
    Filed: October 15, 1979
    Date of Patent: January 27, 1981
    Inventors: Carl E. Barnes, Arthur C. Barnes
  • Patent number: 4247685
    Abstract: A process for forming polymers of 2-pyrrolidone in pellet form via bulk polymerization is disclosed. Polymerization accelerators are empolyed to markedly shorten the polymerization time thus making possible a compact continuous polymerization apparatus which produces pellets of high polymer content requiring no further polymerization. The pellets are formed by forcing the polymerizing mixture through small tubes to form rods of polymer which are then cut into short lengths.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: January 27, 1981
    Inventors: Carl E. Barnes, Arthur C. Barnes
  • Patent number: 4245086
    Abstract: N-Hydroxyalkyltrimellitic acid imides of high purity are prepared by reacting trimellitic acid anhydride with a monoalkanolamine in an aqueous medium comprising an amount of not less than about 0.025 liter of a certain specific solvent or solvent mixture per 1 mole of the trimellitic acid anhydride and can be advantageously used for production of their polymers having a high thermal stability and a good color tone.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: January 13, 1981
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Keiichi Uno, Takahito Miyagawa
  • Patent number: 4233433
    Abstract: Molded articles of polymerized lactams are prepared by pumping of a catalyst containing partial lactam melt at a temperature of .+-. 1.degree. C. of a temperature in the range of 160.degree. C. to 170.degree. C. and a lower temperature activator containing partial lactam melt at a temperature of .+-. 1.degree. C. of a temperature in the range of 160.degree. C. to 170.degree. C. to which activator addition is delayed relative to catalyst addition, with separate gear pumps to a mixing zone maintained between 170 and 175.degree. C., the pumps connected to the mixing zone by straight feed tubes positioned at an angle of inclination to the horizontal of a maximum of 10.degree., each feed tube having a volume of at least one-third greater than the pump to which it is connected and form the mixing zone into a mold. At least part of the gases released are returned to themixing zone by the tube systems and gear pumps. Apparatus to carry out the method is also provided.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: November 11, 1980
    Assignee: Harwe AG
    Inventor: Werner Hartmann
  • Patent number: 4218557
    Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by: ##STR2## wherein Y is selected from the group consisting of ##STR3## and --SO.sub.2 -- and p=0 or 1; when p=0, R.sub.1 and R.sub.2 are independently selected from a group consisting of substituted or unsubstituted aliphatic, aryl, araryl, and alkylaryl radicals or R.sub.1 and R.sub.2 can form a cyclic amide containing radical wherein R.sub.1 and R.sub.2 taken together are selected from a group consisting of --CH.sub.2).sub.n where n=2 to 12, wherein R.sub.3 is a lower alkyl radical or hydrogen; and when p=1, R.sub.1 and R.sub.2 taken together form a linkage in a cyclic imide containing radical selected from a group consisting of --CH.sub.2).sub.n, where n'=2 or 3 and ##STR4## where R.sub.3 is as defined above, R.sub.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: August 19, 1980
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, Adel F. Halasa
  • Patent number: 4218558
    Abstract: The process of making a catalyst for the polymerization of 2-pyrrolidone by contacting an alkali metal pyrrolidonate, a quaternary ammonium carboxylate and carbon dioxide.
    Type: Grant
    Filed: May 5, 1978
    Date of Patent: August 19, 1980
    Assignee: Chevron Research Company
    Inventor: Robert Bacskai
  • Patent number: 4217442
    Abstract: There is disclosed the use of certain quaternary ammonium sulfates and bisulfates as polymerization accelerators in the polymerization of 2-pyrrolidone employing alkali metal pyrrolidonates as primary catalysts together with CO.sub.2, SO.sub.2 or MoO.sub.3 as activators. Methods for recycling both the unchanged monomer and the accelerator are disclosed.The structural formula for the operable quaternary ammonium salts is: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are alkyl, aryl and aralkyl radicals, including mixtures thereof, and n is 1 or 2 depending on the valence of X, and X is a bisulfate or sulfate.In addition to accelerating the rate of polymerization these substances also act as color suppressors when SO.sub.2 is used as the activator. For this purpose X in the above formula may also be a halide. Less than 0.01 mol per mol of alkali metal pyrrolidonate is needed in this use.Cesium or rubidium pyrrolidonates are also disclosed as color suppressors when using SO.sub.2 as the activator.
    Type: Grant
    Filed: May 17, 1979
    Date of Patent: August 12, 1980
    Inventors: Carl E. Barnes, Arthur C. Barnes
  • Patent number: 4195163
    Abstract: Processes for the production of polyamides by polymerizing lactams in the presence of a catalyst and anisocyanatoallophanate as activator.
    Type: Grant
    Filed: October 16, 1978
    Date of Patent: March 25, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf-Volker Meyer, Rolf Dhein, Friedrich Fahnler
  • Patent number: 4191819
    Abstract: A process for the activated anionic polymerization of lactams wherein as activator a fluid partially masked aliphatic araliphatic or cycloaliphatic polyisocyanate being masked with 0.5-0.7 equivalents of lactam per equivalent of NCO groups is used.
    Type: Grant
    Filed: August 12, 1977
    Date of Patent: March 4, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf-Volker Meyer, Rolf Dhein, Kurt Schneider, Friedrich Fahnler
  • Patent number: 4188478
    Abstract: Novel polyamides are prepared having end groups especially selected to impart special properties to the polymer. These polyamides are prepared by utilizing anionic polymerization processes and the end groups can be of a type that, under existing methods, normally will hinder or completely stop the anionic polymerization reaction. The hindering effect of these end groups is largely overcome through the formation of novel initiator compounds that enables the polymerization reaction to proceed with extreme rapidity at comparatively low temperatures despite the presence of these end groups.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: February 12, 1980
    Assignee: The Polymer Corporation
    Inventor: Charles V. Goebel, Jr.
  • Patent number: 4181793
    Abstract: Disclosed is a poly(hydrazone-hydrazide) prepared from difunctional acid chlorides and 4-(hydrazonomethyl)benzoic acid hydrazide. The poly(hydrazone-hydrazide) contains repeating units corresponding to the structure: ##STR1## Films of this polymer have unobviously high tensile and tear strengths without the necessity of biaxially orienting the film.
    Type: Grant
    Filed: August 7, 1978
    Date of Patent: January 1, 1980
    Assignee: Eastman Kodak Company
    Inventor: Harry R. Musser
  • Patent number: 4180650
    Abstract: Processes for the anionic polymerization of lactam accelerated by the presence of nitrothiophene and certain derivatives thereof. The processes are especially applicable to the preparation of poly-2-pyrrolidone which can be molded into filaments, films, and shaped articles in general.
    Type: Grant
    Filed: April 21, 1978
    Date of Patent: December 25, 1979
    Assignee: Chevron Research Company
    Inventor: Henry Y. Lew
  • Patent number: 4172938
    Abstract: An aromatic polyamide having a high degree of polymerization is produced by polymerizing(A) a mixture of an aromatic diamine of the formula (1):H.sub.2 N--Ar.sub.1 --NH.sub.2 (1)and an aromatic dicarboxylic acid dihalide of the formula (2):XOC--Ar.sub.2 --COX (2)(b) a mixture of the aromatic diamine of the formula (1), the aromatic dicarboxylic acid dihalide of the formula (2) and a hydrogen halide salt of an aromatic amino carboxylic acid halide of the formula (3):XH.multidot.H.sub.2 N--Ar.sub.3 --COX (3)or(C) the hydrogen halide salt of the aromatic amino carboxylic acid halide of the formula (3) alone,Wherein Ar.sub.1, Ar.sub.2 and Ar.sub.
    Type: Grant
    Filed: June 13, 1977
    Date of Patent: October 30, 1979
    Assignee: Teijin Limited
    Inventors: Hiroshi Mera, Yasuo Nakagawa, Masahiro Yamaguchi, Mitsuyuki Ohno
  • Patent number: 4171425
    Abstract: Processes for the anionic polymerization of lactam accelerated by the presence of nitrobenzene and/or certain derivatives thereof. The processes are especially applicable to the preparation of poly-2-pyrrolidone which can be molded into filaments, films, and shaped articles in general.
    Type: Grant
    Filed: April 21, 1978
    Date of Patent: October 16, 1979
    Assignee: Chevron Research Company
    Inventor: Henry Y. Lew
  • Patent number: 4163088
    Abstract: The invention relates to antistatic polyamide compositions comprising a polyamide and as an antistatic agent from 0.1 to 20%, preferably from 1.5 to 15%, by weight based on the total weight of the composition of urethanes with ether groups. The urethanes with ether groups are stable in melts of aliphatic polyamides for prolonged periods at temperatures of up to about 300.degree. C. and filaments and fibers of such polyamides or woven fabrics, knitted fabrics, non-woven or pile fabrics produced from these filaments or fibers show outstanding antistatic properties.
    Type: Grant
    Filed: June 20, 1977
    Date of Patent: July 31, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans E. Kunzel, Claus-Rudiger Bernert, Gunter Arend, Francis Bentz, Helmut Sinner, Dieter Brokmeier
  • Patent number: 4139696
    Abstract: 2-Pyrrolidone is continuously polymerized to a high-molecular-weight particulate product by the stirred polymerization of the carbonated alkaline polymerizate. The polymerizate is prepared by contacting an aqueous hydroxide with excess 2-pyrrolidone, maintaining the resultant alkaline mixture at an elevated temperature for sufficient time to reduce the 2-pyrrolidone dimer content of the mixture to within the desired limits, dehydrating the alkaline mixture to reduce the water content to within the desired limits, and contacting the alkaline mixture with carbon dioxide to form the carbonated alkaline polymerizate. The paste of particular polypyrrolidone and liquid polymerizate is continuously withdrawn from the reactor, neutralized with aqueous acid and washed with warm water.
    Type: Grant
    Filed: April 29, 1977
    Date of Patent: February 13, 1979
    Assignee: Chevron Research Company
    Inventors: Byron E. Anshus, Kiyoshi Katsumoto, Ira M. Serkes
  • Patent number: 4107154
    Abstract: Copolymers of 2-pyrrolidone and C.sub.7 -C.sub.12 lactams are provided in solid form, at relatively high rates and molecular weights by polymerization in the presence of alkaline catalysts and carbon dioxide, by the inclusion of an auxiliary catalyst and a copolymerization promoter comprising certain onium salts and N-acyl lactams, respectively.
    Type: Grant
    Filed: March 2, 1977
    Date of Patent: August 15, 1978
    Assignee: Chevron Research Company
    Inventor: Robert Bacskai
  • Patent number: 4105644
    Abstract: The invention relates to a method for manufacturing of anionic polycaprolactam with a low content of water extractables and high stability of the degree of polymerization during melting by a two-stage polymerization using known basic initiators and known activators of the following types: ##STR1## where R is ##STR2## R.sup.1 = R or C.sub.1-4 alkyl, cycloalkyl or allyl, R.sup.2 = C.sub.1-4 alkyl or H atom, n is an integer 3-11 and x is an integer >3. The ratio of activator to initiator (e.g. sodium dihydromethoxyethoxyaluminate) ranges between 2.6 and 4.2, advantageously 2.8-3.5 The first polymerization stage proceeds at 150.degree.-200.degree. C. for .ltoreq.10 min, the polymer is then shaped and postpolymerized at 150.degree.-200.degree. C. for .ltoreq.90 min to achieve a monomer content near to the equilibrium content corresponding to the 2nd stage temperature.
    Type: Grant
    Filed: July 1, 1976
    Date of Patent: August 8, 1978
    Assignee: Ceskoslovenska akademie ved
    Inventors: Zbynek Bukac, Jan Sebenda, Miloslav Loyda
  • Patent number: 4104324
    Abstract: The invention is related to novel polycaprolactam filaments and fibres capable of being deeply dyed with acid dyes to give dye finishes with extreme fastness to light, characterized by the fact that they consist of physical mixtures of unmodified polycaprolactam and a basic polycaprolactam containing structural units corresponding to the formula: ##STR1## in which R represents an alkylene radical with 4 to 12 carbon atoms and x is an integer from 1 to 5, have relative solution viscosities of from 2.9 to 3.5 (as measured on solutions of 1 g of non-extracted polyamide in 100 ml of cresol at 25.degree. C) and contain free amino groups in a concentration range from 60 to 180 millivals per kg of polymer mixture.
    Type: Grant
    Filed: September 21, 1977
    Date of Patent: August 1, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eduard Radlmann, Hans-Georg Gelhaar, Gunther Nischk
  • Patent number: 4101447
    Abstract: The process of making a catalyst for the polymerization of 2-pyrrolidone by contacting an alkali metal pyrrolidonate, a quaternary ammonium carboxylate and carbon dioxide.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: July 18, 1978
    Assignee: Chevron Research Company
    Inventor: Robert Bacskai