Organic Phosphorus Compound Contains A Phosphorus Atom Bonded To An Atom Other Than Oxygen Patents (Class 521/108)
  • Patent number: 4334031
    Abstract: In the preparation of conventional or high resiliency flexible polyurethane flame retarded foams by reacting organic polyisocyanates with polyols containing vinylic polymers and employing flame retardant compounds, less flame retardant compound is required to pass the California Bulletin No. 117 flame test when the particle size of the vinylic polymers is greater than 0.5 microns.
    Type: Grant
    Filed: January 12, 1981
    Date of Patent: June 8, 1982
    Assignee: BASF Wyandotte Corporation
    Inventors: Jay G. Otten, Duane A. Heyman, John R. Murphy
  • Patent number: 4328321
    Abstract: The present invention relates to a process for the preparation of polyurethane foams capable of being flame laminated and high frequency welded, comprising reacting:(a) polyisocyanate,(b) a compound having a molecular weight of from 400 to 10,000 containing at least two isocyanate-reactive hydrogen atoms and(c) a dialkoxy-phosphonyl-N-alkyl-formic acid amide of the formula: ##STR1## wherein m represents an integer of from 1 to 3,n represents an integer of from 0 to 8,X represents halogen, hydrogen, C.sub.1 to C.sub.6 alkyl, --OR, or ##STR2## R represents C.sub.1 to C.sub.6 alkyl, R.sub.1 represents hydrogen, C.sub.1 to C.sub.10 alkyl, C.sub.1 to C.sub.10 alkylene, C.sub.6 to C.sub.10 aryl or C.sub.6 to C.sub.10 arylene, andR.sub.2 and R.sub.3, which may be the same or different, represent C.sub.1 to C.sub.10 alkyl in the presence of water and/or blowing agent.The present invention also relates to dialkoxy-phosphonyl-N-formic acid amides.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: May 4, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Haas, Heinz Muller, Peter Seifert, Kuno Wagner, Kurt Findeisen, Klaus Konig
  • Patent number: 4313761
    Abstract: Reaction products are prepared from metal oxides and salts and phosphorus compounds containing trivalent phosphorus. The reaction products are useful as flame retardants and smoke suppressants.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: February 2, 1982
    Assignee: Monsanto Company
    Inventors: Samuel F. Joyce, III, Albert W. Morgan, Norman W. Touchette, William Vanderlinde
  • Patent number: 4312959
    Abstract: Polyurethane foams exhibiting excellent thermal and oxidative stability can be prepared using as the polymerization or gel catalyst a composition containing at least one organotin compound containing phosphorus and at least one organotin compound wherein a halogen atom is bonded to tin or phosphorus. The terminal properties of foams obtained using the present catalyst compositions are superior to those exhibited by foams prepared using gel catalyst compositions wherein tin, phosphorus and a halogen are present but the phosphorus and halogen are not in the same molecule as the tin atom. The halogen containing tin compound and the phosphorus-containing tin compound may be identical or different. The recovery properties of the foam can be improved by the presence of a carboxylic acid in the catalyst composition.
    Type: Grant
    Filed: February 17, 1981
    Date of Patent: January 26, 1982
    Assignee: M&T Chemicals Inc.
    Inventors: Kenneth Treadwell, Emily C. Bossert
  • Patent number: 4292412
    Abstract: This invention relates to new, hydrophilic, fabric softener foam compositions having improved release ability of the fabric softener abetted by the addition of a hydrophilic polyether polyol release agent to the aqueous reactant containing the fabric softener prior to reacting the aqueous reactant with a hydrophilic, isocyanate-terminated prepolymer to form the foam.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: September 29, 1981
    Assignee: W. R. Grace & Co.
    Inventor: Louis L. Wood
  • Patent number: 4291129
    Abstract: A low reactive pressure flame-retardant polyurethane foam made by reacting together a polymeric isocyanate, a polyol, an aqueous solution of a carbohydrate, calcium acid phosphate, sodium aluminum sulfate, sodium bicarbonate, and a flame retardant. A blowing agent may be present.
    Type: Grant
    Filed: June 25, 1980
    Date of Patent: September 22, 1981
    Assignees: Patrick James. Crehan, Richard J. Fricke
    Inventor: Richard B. Kennedy
  • Patent number: 4275171
    Abstract: This invention is directed to a process for producing flame retardant flexible polyurethane foams having a porosity in the range between 0.5 and 10 cubic feet per minute. A polyol having an average molecular weight between about 250 and about 6,500 is reacted with toluene diisocyanate which comprises a mixture of the isomers of 2,4- and 2,6- toluene diisocyanate. The concentration of 2,4- toluene diisocyanate isomer is not critical. The formulation of the present invention includes a flame retardant mixture of a plasticizer and dibromoneopentyl glycol. The plasticizer is either a halogenated phosphonate or halogenated phosphate ester. Chlorine is the preferred halogen atom. The weight ratio of those ingredients is between about 50/50 and about 90/10 with the ratio 85/15 preferred. The concentration of that mixture is from about 1 to about 20 percent by weight of the polyol.
    Type: Grant
    Filed: April 12, 1979
    Date of Patent: June 23, 1981
    Assignee: Reeves Brothers, Inc.
    Inventor: Gunter H. Wegner
  • Patent number: 4273881
    Abstract: High-resiliency flexible polyurethane foams having at least a 10 percent vinylic polymer or copolymer content may be rendered flame retardant by incorporating therein effective amounts of ANTIBLAZE 19, reputed to have the following structure ##STR1## wherein x is equal to 0 or 1. This compound is also synergistic with other flame-retardant compounds.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Wyandotte Corporation
    Inventor: Jay G. Otten
  • Patent number: 4263411
    Abstract: A process of forming polyurethane compositions which emit reduced amounts of toxic smoke on burning is described. The process comprises reacting a mixture of an organic compound having two or more active hydrogen atoms, an organic polyfunctional isocyanate, a catalyst and at least one metal salt of an aliphatic or alicyclic monocarboxylic acid wherein the metal is cobalt, copper, nickel or manganese. The metal salt is added to the mixture in an amount which is sufficient to reduce the formation of toxic substances when the polyurethane is ignited.
    Type: Grant
    Filed: September 28, 1979
    Date of Patent: April 21, 1981
    Assignee: Mooney Chemicals, Inc.
    Inventor: Eugene Bak
  • Patent number: 4255526
    Abstract: A moisture- and heat-resistant flexible polyurethane foam, which is free from lowering of the foam hardness due to moisture absorption during or after the production of the foam under a high temperature and high humidity condition and free from development of scorch during the production of the foam, can be obtained by adding an amino acid or an amino acid analogous compound to a raw material mixture, and foaming the resulting mixture.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: March 10, 1981
    Assignee: Bridgestone Tire Company Limited
    Inventors: Toshio Yukuta, Hiroya Fukuda, Seiji Ishii
  • Patent number: 4250005
    Abstract: Polyurethane foams having modified properties, such as increased tensile strength, tear strength and improved compression-deflection characteristics are prepared by incorporating in a foam-forming composition, an effective amount of a cross-link promoter, selected from the group consisting of polyfunctional, polyunsaturated acrylates; polyfunctional, polyunsaturated methacrylates; triallyl cyanurate; methyl methacrylate; 1,5-cyclooctadiene and bis (.beta.-chloroethyl) vinyl phosphonate. After a foam is prepared from the composition, it is exposed to a radiation dosage sufficient to modify the properties of said foam.
    Type: Grant
    Filed: August 20, 1976
    Date of Patent: February 10, 1981
    Assignee: Scott Paper Company
    Inventor: Roland J. Lamplugh
  • Patent number: 4246360
    Abstract: A flexible polyurethane foam is provided which is fire retardant and non-dripping upon exposure to flame. The flexible polyurethane foam is prepared by the reaction of a polyol, an isocyanate and a protein.
    Type: Grant
    Filed: July 22, 1977
    Date of Patent: January 20, 1981
    Assignee: Monsanto Company
    Inventors: Jasper H. Brown, Albert W. Morgan
  • Patent number: 4242497
    Abstract: Poly(aldehyde amino silicate) foams are produced by mixing an amino compound, an aldehyde, a silicon oxide compound and a blowing agent; then a curing agent is added, thereby producing a rigid, porous product.
    Type: Grant
    Filed: January 10, 1980
    Date of Patent: December 30, 1980
    Inventor: David H. Blount
  • Patent number: 4234696
    Abstract: The present invention relates to 2-chloroethylphosphonate mixtures which are effective flame retardants for organic polymeric materials and have especially beneficial effects on rise and tack-free times in the production of rigid polyurethane foams.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: November 18, 1980
    Assignee: Monsanto Company
    Inventors: Gail H. Birum, Richard F. Jansen
  • Patent number: 4234694
    Abstract: Addition compounds based on:(a) phospholine oxides, phospholine sulphides, phospholane oxides or phospholane sulphides, and(b) mono-, di- and/or polyalcohols with a molecular weight of 32 to 250 or protonic acids whose N/10 aqueous solutions have a pH of between 1 and 8 or metal salts or acid chlorides are disclosed. These addition compounds are useful as catalysts for the preparation of carbodiimides, particularly carbodiimide foams which have improved properties.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: November 18, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andrea La Spina, Werner Dietrich, Reinhard Schliebs
  • Patent number: 4230822
    Abstract: Improved hydrophilic crosslinked polyurethane foams are prepared by reacting (a) an isocyanate-capped polyoxyethylene prepolymer with (b) at least 20 moles of water per mole of NCO groups in the presence of (c) alumina hydrate, (d) a phosphorus fire-retardant additive and (e) an organic carbon compound which serves to react with phosphate anions at high temperatures (e.g., in the presence of a flame) and reinforces the char provided by combustion of the foam.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: October 28, 1980
    Assignee: W. R. Grace & Co.
    Inventors: Robert M. Murch, Phyllis I. Meyer, John J. Eagan
  • Patent number: 4221874
    Abstract: The present invention relates to a process for the improvement of the flame retardant properties of a polymer composition which comprises incorporating therein an effective flame retardant amount of a halogenated phospholane oxide. The resultant products are useful as rigid or flexible foams and shaped articles having greatly improved flame retardant and smoke suppressant properties. The use of the halogenated phospholane oxide also imparts stability to the products, thus overcoming difficulties encountered with volatile phosphorus compounds which had been used heretofore with polymeric compositions such as polyurethanes.
    Type: Grant
    Filed: June 7, 1978
    Date of Patent: September 9, 1980
    Assignee: Monsanto Company
    Inventor: Kurt Moedritzer
  • Patent number: 4221877
    Abstract: Covers a water-modified diisocyanate mixture obtained from water-treating a diphenylmethane diisocyanate to provide a diisocyanate mixture comprising 3-25 percent by weight of diphenylmethane biuret isocyanate and 75-97 percent diphenylmethane diisocyanate. Also covers the use of said water-modified diphenylmethane diisocyanate in preparing an improved polyurethane or polyisocyanurate polymer. Also covers said polymers.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: September 9, 1980
    Assignee: Texaco Development Corp.
    Inventors: Michael Cuscurida, Robert L. Zimmerman, Bobbie J. Ramey, deceased
  • Patent number: 4207417
    Abstract: Polyhydroxylated O,O-dialkyl phosphonoacetals having the formula ##STR1## wherein R is an alkyl group having from 1-3 carbon atoms;n is an integer from 1-2;q is an integer from 1-3;R' is a residue of a polyhydroxy compound having from 5-12 carbon atoms;m is an integer from 2-6, useful as polyol reactants in the preparation of flame-retardant polyurethanes, are prepared by trans-acetalating a low molecular weight O,O-dialkyl phosphonoacetal with a polyhydroxy compound under acid catalysis.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: June 10, 1980
    Assignee: Yeda Research & Development Co. Ltd.
    Inventors: David Vofsi, Martin M. Halmann, Saul Yanai
  • Patent number: 4196155
    Abstract: A process for preparing an organic phosphorous compound of the general formula ##STR1## wherein R.sub.A represents ##STR2## where X.sup.1 is a halogen atom, Y is --CH.sub.2 -- or --CH.sub.2 --C.sub.2 --, andR.sub.1 is H or CH.sub.3 when Y is --CH.sub.2 --CH.sub.2 --, or H, CH.sub.3 or C.sub.2 H.sub.5 when Y is --CH.sub.2 --,R.sub.B represents an alkyl group having from 1 to 4 carbon atoms or a halogenated alkyl group having from 2 to 4 carbon atoms,R.sub.C represents ##STR3## where X.sup.2 is a halogen atom, Z is --CH.sub.2 --or --CH.sub.2 --CH.sub.2 --, andR.sub.2 is H or CH.sub.3 when Z is --CH.sub.2 --CH.sub.2 --, or H, CH.sub.3 or C.sub.2 H.sub.5 when Z is --CH.sub.2 --, andR.sub.D represents an alkyl group having from 1 to 4 carbon atoms or a halogenated alkyl group having from 2 to 4 carbon atoms,the process including the steps of reacting a cyclic halogenophosphite with a cyclic phosphorous acid and acetone in a molar ratio of 1:1:1, reacting the resulting product with a molecular halogen X.sub.2.sup.
    Type: Grant
    Filed: June 27, 1978
    Date of Patent: April 1, 1980
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Isamu Yamamoto, Eiichi Noda, Yoshiaki Noguchi
  • Patent number: 4194068
    Abstract: Liquid flame-retardants for polyurethane compositions are disclosed. The liquid flame-retardants contain a mixture of a bromohydrin of pentaerythritol, a polyhydric alcohol, and a sufficient amount of a flame-retardant organo-phosphorus compound to render the mixture a substantially solids-free liquid at 25.degree. C., one atmosphere pressure. Illustrative of these flame-retardants is a solution of 2,2-bis(bromomethyl)-1,3-propanediol, a cyclic phosphonate ester of the formula ##STR1## where x=0 or 1, and a poly(oxypropylene) adduct of glycerol having an average molecular weight of about 300.
    Type: Grant
    Filed: March 21, 1978
    Date of Patent: March 18, 1980
    Assignee: The Dow Chemical Company
    Inventors: Dennis P. Miller, Masahiko Tamaki
  • Patent number: 4185147
    Abstract: Poly(aldehyde amino silicate) foams are produced by mixing an amino compound, an aldehyde, a silicon oxide compound and a blowing agent; then a curing agent is added, thereby producing a rigid, porous product.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: January 22, 1980
    Inventor: David H. Blount
  • Patent number: 4179482
    Abstract: The present invention relates to 2-chloroethylphosphonate mixtures which are effective flame retardants for organic polymeric materials and have especially beneficial effects on rise and tack-free times in the production of rigid polyurethane foams.
    Type: Grant
    Filed: September 25, 1978
    Date of Patent: December 18, 1979
    Assignee: Monsanto Company
    Inventors: Gail H. Birum, Richard F. Jansen
  • Patent number: 4163767
    Abstract: A polyphosphorous mixed phosphite-phosphonate polymer flame retardant having an OH number less than one and containing both alkyl phosphite and haloalkyl phosphonate linkages.
    Type: Grant
    Filed: January 30, 1978
    Date of Patent: August 7, 1979
    Assignee: Stauffer Chemical Company
    Inventor: Silvio L. Giolito
  • Patent number: 4147710
    Abstract: A compound adapted to be used to advantage as a catalyst for making carbodiimide foams is prepared by a process wherein(a) a phosphetane oxide or phosphetane sulphide of the general Formulae I and II: ##STR1## wherein X represents a C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.6 -C.sub.14 aryl, C.sub.7 -C.sub.20 aralkyl, C.sub.1 -C.sub.18 alkoxy or C.sub.6 -C.sub.14 aroxy group andR.sup.1 to R.sup.6 represent hydrogen and/or C.sub.1 -C.sub.4 alkyl groups and is reacted with(b) a mono-, di- and/or polyhydric alcohol having a molecular weight of about 32 to about 250, a protonic acid which has a pH of between 1 and 8 in N/10 aqueous solution, a metal salt or an acid chloride.
    Type: Grant
    Filed: September 23, 1975
    Date of Patent: April 3, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andrea La Spina, Werner Dietrich, Reinhard Schliebs
  • Patent number: 4144387
    Abstract: There is provided a flame retardant mixture containing between about one weight percent and about 75 weight percent of a compound having the structure: ##STR1## AND BETWEEN ABOUT 99 WEIGHT PERCENT AND ABOUT 25 WEIGHT PERCENT OF A HIGH BOILING PHOSPHONATE COMPRISING PREDOMINANTLY A COMPOUND HAVING THE STRUCTURE: ##STR2## There are also provided polymers, particulary rigid and flexible urethane foams, containing between about two weight percent and about 30 weight percent of the flame retardant mixture.
    Type: Grant
    Filed: February 2, 1978
    Date of Patent: March 13, 1979
    Assignee: Mobil Oil Corporation
    Inventors: James J. Anderson, Vasco G. Camacho, Robert E. Kinney, Francis M. Seger
  • Patent number: 4133823
    Abstract: Reaction products are prepared from metal oxides and salts and phosphorus compounds containing trivalent phosphorus. The reaction products are useful as flame retardants and smoke suppressants.
    Type: Grant
    Filed: September 17, 1976
    Date of Patent: January 9, 1979
    Assignee: Monsanto Company
    Inventors: Samuel F. Joyce, III, Albert W. Morgan, Norman W. Touchette, William Vanderlinde
  • Patent number: 4129694
    Abstract: The invention disclosed relates to a new fabric softener foam having improved utility for softening textile fabrics in either a standard or automatic clothes dryer as well as in an automatic washer.
    Type: Grant
    Filed: April 7, 1976
    Date of Patent: December 12, 1978
    Assignee: W. R. Grace & Co.
    Inventors: Joseph A. Cogliano, Clifton L. Kehr
  • Patent number: 4129695
    Abstract: Polymers comprising polyoxazolidone and carbodiimide recurring units of the formula: ##STR1## are prepared from polyisocyanates and polyepoxides. Non-friable, low density fire resistant foams are prepared directly from the polymers of the invention without the equisite addition of pore-forming agents.
    Type: Grant
    Filed: March 16, 1977
    Date of Patent: December 12, 1978
    Assignee: Rhone-Poulenc Industries
    Inventor: Yves Bonin
  • Patent number: 4113669
    Abstract: 2-Oxo-2-alkoxy-5-dialkylphosphono-1,2-oxaphospholanes of the formula ##STR1## in which R.sub.1 to R.sub.7 are hydrocarbon radicals can be prepared from .alpha.,.beta.-unsaturated ketones and 2 or more moles of a dialkyl phosphite. Obviously .gamma.-ketophosphonates are intermediates of this reaction, as these compounds react with 1 or more moles of dialkyl phosphite in yielding the oxaphospholanes too. Both reactions are promoted by alkaline catalysts.The new oxaphospholane derivatives are considerably stable against thermal decomposition. They are compatible with polymeric materials and can be used as flame protecting agent for plastics and resins, for example, in polyurethane foams.
    Type: Grant
    Filed: June 13, 1977
    Date of Patent: September 12, 1978
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Zondler, Emil Saladin, Rudolf Kirchmayr
  • Patent number: 4113671
    Abstract: Carbamates of diethyl methylphosphonate of the formula: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are linear or branched alkyl or hydroxyalkyl radicals containing 2 or 3 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a ring containing 4 or 5 carbon atoms, or R.sub.1 is phenyl and R.sub.2 is hydrogen, may be prepared by reacting diethyl hydroxymethyl-phosphonate chloroformate with an amine, and find application in flameproofing rigid or flexible polyurethane foams.
    Type: Grant
    Filed: October 3, 1977
    Date of Patent: September 12, 1978
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Serge L. Lecolier, Jean-Marie J. Biehler
  • Patent number: 4111828
    Abstract: Stable mixtures, comprising a sucrose-based polyol, a .beta.-haloalkyl phosphate or .beta.-haloalkyl phosphonate flame retardant and a hydroxylamine catalyst are provided which are characterized by prolonged shelf life. The stable mixtures are used in the preparation of foamed urethane polymers by reaction thereof with an isocyanate. The urethane polymers are useful as flexible foam insulating material in buildings, pipe lines, storage tanks and refrigerators and as flexible foams in cushions, mattresses, carpet backings, and packaging materials.
    Type: Grant
    Filed: January 3, 1977
    Date of Patent: September 5, 1978
    Assignee: Monsanto Company
    Inventor: Donald S. T. Wang
  • Patent number: 4108833
    Abstract: Silicone rubber compositions comprising (A) a diorganopolysiloxane in which the organo substituents are 0.01 to 2 mole % vinyl groups, 0 to 10 mole % phenyl groups and the remainder is alkyl groups, (B) an organohydrogenpolysiloxane, (C) a (O) valent platinum-(III) phosphor complex and, optionally, (D) a filler. These compositions can be cured with steam. Foamable composition comprising (A), (B), (C) and hydrophobicized wet-process silica.
    Type: Grant
    Filed: November 18, 1976
    Date of Patent: August 22, 1978
    Assignee: Toshiba Silicone Co., Ltd.
    Inventors: Masayuki Hatanaka, Makoto Matsumoto, Masaharu Yonezawa
  • Patent number: 4101472
    Abstract: Novel diesters of diethyl hydroxymethylphosphonate of the formula: ##STR1## in which R.sub.1 and R.sub.4 are alkylene radicals --(CH.sub.2).sub.m -- in which m is 0 or an integer; R.sub.2 and R.sub.3 are H or alkyl radicals, the total number of carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 being not more than 10, are described.These diesters are valuable flameproofing agents for rigid and flexible polyurethane foams and for thermoplastic polyolefin and polyester foams.
    Type: Grant
    Filed: November 1, 1976
    Date of Patent: July 18, 1978
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Jean-Marie J. Biehler, Serge L. Lecolier, Patrice M. Le Roy