Organic Phosphorus Compound Contains A Phosphorus Atom Bonded To An Atom Other Than Oxygen Patents (Class 521/108)
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Patent number: 4334031Abstract: 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: GrantFiled: January 12, 1981Date of Patent: June 8, 1982Assignee: BASF Wyandotte CorporationInventors: Jay G. Otten, Duane A. Heyman, John R. Murphy
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Patent number: 4328321Abstract: 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: GrantFiled: September 11, 1980Date of Patent: May 4, 1982Assignee: Bayer AktiengesellschaftInventors: Peter Haas, Heinz Muller, Peter Seifert, Kuno Wagner, Kurt Findeisen, Klaus Konig
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Patent number: 4313761Abstract: 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: GrantFiled: October 24, 1980Date of Patent: February 2, 1982Assignee: Monsanto CompanyInventors: Samuel F. Joyce, III, Albert W. Morgan, Norman W. Touchette, William Vanderlinde
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Patent number: 4312959Abstract: 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: GrantFiled: February 17, 1981Date of Patent: January 26, 1982Assignee: M&T Chemicals Inc.Inventors: Kenneth Treadwell, Emily C. Bossert
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Patent number: 4292412Abstract: 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: GrantFiled: January 16, 1980Date of Patent: September 29, 1981Assignee: W. R. Grace & Co.Inventor: Louis L. Wood
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Patent number: 4291129Abstract: 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: GrantFiled: June 25, 1980Date of Patent: September 22, 1981Assignees: Patrick James. Crehan, Richard J. FrickeInventor: Richard B. Kennedy
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Patent number: 4275171Abstract: 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: GrantFiled: April 12, 1979Date of Patent: June 23, 1981Assignee: Reeves Brothers, Inc.Inventor: Gunter H. Wegner
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Patent number: 4273881Abstract: 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: GrantFiled: December 3, 1979Date of Patent: June 16, 1981Assignee: BASF Wyandotte CorporationInventor: Jay G. Otten
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Patent number: 4263411Abstract: 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: GrantFiled: September 28, 1979Date of Patent: April 21, 1981Assignee: Mooney Chemicals, Inc.Inventor: Eugene Bak
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Patent number: 4255526Abstract: 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: GrantFiled: August 27, 1979Date of Patent: March 10, 1981Assignee: Bridgestone Tire Company LimitedInventors: Toshio Yukuta, Hiroya Fukuda, Seiji Ishii
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Patent number: 4250005Abstract: 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: GrantFiled: August 20, 1976Date of Patent: February 10, 1981Assignee: Scott Paper CompanyInventor: Roland J. Lamplugh
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Patent number: 4246360Abstract: 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: GrantFiled: July 22, 1977Date of Patent: January 20, 1981Assignee: Monsanto CompanyInventors: Jasper H. Brown, Albert W. Morgan
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Patent number: 4242497Abstract: 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: GrantFiled: January 10, 1980Date of Patent: December 30, 1980Inventor: David H. Blount
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Patent number: 4234696Abstract: 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: GrantFiled: April 6, 1979Date of Patent: November 18, 1980Assignee: Monsanto CompanyInventors: Gail H. Birum, Richard F. Jansen
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Patent number: 4234694Abstract: 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: GrantFiled: May 21, 1979Date of Patent: November 18, 1980Assignee: Bayer AktiengesellschaftInventors: Andrea La Spina, Werner Dietrich, Reinhard Schliebs
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Patent number: 4230822Abstract: 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: GrantFiled: October 10, 1978Date of Patent: October 28, 1980Assignee: W. R. Grace & Co.Inventors: Robert M. Murch, Phyllis I. Meyer, John J. Eagan
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Patent number: 4221874Abstract: 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: GrantFiled: June 7, 1978Date of Patent: September 9, 1980Assignee: Monsanto CompanyInventor: Kurt Moedritzer
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Patent number: 4221877Abstract: 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: GrantFiled: January 27, 1978Date of Patent: September 9, 1980Assignee: Texaco Development Corp.Inventors: Michael Cuscurida, Robert L. Zimmerman, Bobbie J. Ramey, deceased
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Patent number: 4207417Abstract: 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: GrantFiled: December 8, 1977Date of Patent: June 10, 1980Assignee: Yeda Research & Development Co. Ltd.Inventors: David Vofsi, Martin M. Halmann, Saul Yanai
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Patent number: 4196155Abstract: 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: GrantFiled: June 27, 1978Date of Patent: April 1, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Isamu Yamamoto, Eiichi Noda, Yoshiaki Noguchi
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Patent number: 4194068Abstract: 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: GrantFiled: March 21, 1978Date of Patent: March 18, 1980Assignee: The Dow Chemical CompanyInventors: Dennis P. Miller, Masahiko Tamaki
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Patent number: 4185147Abstract: 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: GrantFiled: October 27, 1978Date of Patent: January 22, 1980Inventor: David H. Blount
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Patent number: 4179482Abstract: 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: GrantFiled: September 25, 1978Date of Patent: December 18, 1979Assignee: Monsanto CompanyInventors: Gail H. Birum, Richard F. Jansen
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Patent number: 4163767Abstract: 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: GrantFiled: January 30, 1978Date of Patent: August 7, 1979Assignee: Stauffer Chemical CompanyInventor: Silvio L. Giolito
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Patent number: 4147710Abstract: 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: GrantFiled: September 23, 1975Date of Patent: April 3, 1979Assignee: Bayer AktiengesellschaftInventors: Andrea La Spina, Werner Dietrich, Reinhard Schliebs
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Patent number: 4144387Abstract: 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: GrantFiled: February 2, 1978Date of Patent: March 13, 1979Assignee: Mobil Oil CorporationInventors: James J. Anderson, Vasco G. Camacho, Robert E. Kinney, Francis M. Seger
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Patent number: 4133823Abstract: 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: GrantFiled: September 17, 1976Date of Patent: January 9, 1979Assignee: Monsanto CompanyInventors: Samuel F. Joyce, III, Albert W. Morgan, Norman W. Touchette, William Vanderlinde
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Patent number: 4129694Abstract: 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: GrantFiled: April 7, 1976Date of Patent: December 12, 1978Assignee: W. R. Grace & Co.Inventors: Joseph A. Cogliano, Clifton L. Kehr
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Patent number: 4129695Abstract: 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: GrantFiled: March 16, 1977Date of Patent: December 12, 1978Assignee: Rhone-Poulenc IndustriesInventor: Yves Bonin
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Patent number: 4113669Abstract: 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: GrantFiled: June 13, 1977Date of Patent: September 12, 1978Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Emil Saladin, Rudolf Kirchmayr
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Patent number: 4113671Abstract: 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: GrantFiled: October 3, 1977Date of Patent: September 12, 1978Assignee: Societe Nationale des Poudres et ExplosifsInventors: Serge L. Lecolier, Jean-Marie J. Biehler
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Patent number: 4111828Abstract: 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: GrantFiled: January 3, 1977Date of Patent: September 5, 1978Assignee: Monsanto CompanyInventor: Donald S. T. Wang
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Patent number: 4108833Abstract: 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: GrantFiled: November 18, 1976Date of Patent: August 22, 1978Assignee: Toshiba Silicone Co., Ltd.Inventors: Masayuki Hatanaka, Makoto Matsumoto, Masaharu Yonezawa
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Patent number: 4101472Abstract: 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: GrantFiled: November 1, 1976Date of Patent: July 18, 1978Assignee: Societe Nationale des Poudres et ExplosifsInventors: Jean-Marie J. Biehler, Serge L. Lecolier, Patrice M. Le Roy