Reactant Contains At Least One Phosphorus Atom Patents (Class 528/72)
  • Patent number: 4786705
    Abstract: This invention is directed to adducts of a poly(active hydrogen) organic compound and a polyepoxide comprising the reaction product of a poly(active hydrogen) organic compound and a polyepoxide containing two or more epoxy groups per molecule, said poly(active hydrogen) organic compound being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyepoxide. The adducts are useful in the formulation of high solids coating compositions, polyurethane elastomers, inks, sealants, adhesives and the like.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: November 22, 1988
    Assignee: Union Carbide Corporation
    Inventor: Joseph V. Koleske
  • Patent number: 4777189
    Abstract: Flame-retardant polyurethane foam having a very good skin weldability and a very low level of skin staining is produced from a polyhydroxy compound, organic polyisocyanate, blowing agent, catalyst, foam stabilizer, and flame retardant, and other additives, wherein the flame retardant contains a triaryl phosphate ester and the polyhydroxy compound is a mixture composed of 100 parts by weight of high-molecular-weight polyhydroxy compound having a hydroxyl number lower than 100 and 0.5 to 10 parts by weight of low-molecular-weight polyhydroxy compound having a hydroxyl number higher than 560 and having 2 to 4 hydroxyl groups in one molecule.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: October 11, 1988
    Assignees: Ikeda Bussan Co., Ltd., Bridgestone Corporation
    Inventors: Kenji Shimomura, Shigeaki Kouketsu, Toru Okuyama, Take Sato
  • Patent number: 4775740
    Abstract: The subject invention pertains to a novel class of fire- and heat-resistant bisimide resins prepared by thermal polymerization of maleimido or citraconimido substituded 1-[(dialkoxyphosphonyl)-methyl]-2-4 and -2,6-diaminobenzenes. Typical polymer presursors have the chemical structure: ##STR1## wherein R is alkyl, substituted alkyl or aryl, and R.sup.1 is hydrogen or lower alkyl.The polymer precursors are prepared by reacting 1-[(diorganooxyphosphonyl)methyl]-2-4 and -2,6-diaminobenzenes with maleic anhydride or citraconic anhydride in a mole ratio 1:2. Chains extension of the monomers is achieved by reacting the mono-N-maleimido derivatives of 1-[(diorganooxyphosphonyl)methyl]-2,4 and -2,6-diaminobenzenes with aryl tetracarboxylic dianhydrides, such as benzophenone tetracarboxylic diandydride, or aryl diisocyanates, such as methylenebis(4-phenylisocyanate), in a mole ratio 2:1.
    Type: Grant
    Filed: April 10, 1986
    Date of Patent: October 4, 1988
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: James M. Beggs, John A. Mikroyannidis, Demetrius A. Kourtides
  • Patent number: 4743673
    Abstract: Hydrophilic polyurethane polymers having carboxy groups in the polymer backbone are prepared by reacting a polyol component, an ester of a carboxylic acid and a polyisocyanate to form a polyurethane intermediate. The intermediate is then saponified and the saponified product neutralized to form free carboxy groups. The water absorption of the intermediates and saponified polymers is above 10% and the polyurethanes may range from rigid solids to gel-like, high water absorptive polymers. Neutralization of the carboxy group with ammonium hydroxide produces a water soluble polyurethane which becomes water insoluble when the ammonia is driven off. The carboxy groups introduced into the polymeric chain provide reactive sites for attachment of various side-groups and also allow for various curing procedures.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: May 10, 1988
    Assignee: Tyndale Plains-Hunter, Ltd.
    Inventors: Christian W. Johnston, John M. Teffenhart
  • Patent number: 4740527
    Abstract: A porous or non-porous intumescent mass comprising one or more carbonization auxiliaries, one or more fillers and optionally one or more other auxiliary agents, produced by the reaction of a polyisocyanate with an isocyanate reactive compound, optionally containing phosphorus or boron, in the presence of polyepoxide. The intumescent mass according to the invention having good fire characteristics and can be used to produce structural elements for fire resistance purposes, fire barriers, textile coatings, linings, laminates and pipe insulators.
    Type: Grant
    Filed: November 7, 1986
    Date of Patent: April 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wulf von Bonin
  • Patent number: 4729925
    Abstract: Herein are disclosed polyurethane elastomers comprising a charge-control agent of the formula: ##STR1## The elastomers are useful in making shaped articles.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: March 8, 1988
    Assignee: Eastman Kodak Company
    Inventors: Tsang J. Chen, Donald A. Upson, Paul D. Yacobucci
  • Patent number: 4696952
    Abstract: Flame-retardant polyurethane foam having a very good skin weldability and a very low level of skin staining is produced from a polyhydroxy compound, organic polyisocyanate, blowing agent, catalyst, foam stabilizer, and flame retardant, and other additives, wherein the flame retardant contains a triaryl phosphate ester and the polyhydroxy compound is a mixture composed of 100 parts by weight of high-molecular-weight polyhydroxy compound having a hydroxyl number lower than 100 and 0.5 to 10 parts by weight of low-molecular-weight polyhydroxy compound having a hydroxyl number higher than 560 and having 2 to 4 hydroxyl groups in one molecule.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: September 29, 1987
    Assignees: Ikeda Bussan Co., Ltd., Bridgestone Corp.
    Inventors: Kenji Shimomura, Shigeaki Kouketsu, Toru Okuyama, Take Sato
  • Patent number: 4680368
    Abstract: An ultraviolet curable ink composition comprising, as main components,(A) a polyurethane poly(meth)acrylate obtained by reacting a polyisocyanate compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a methyl group, and n is an integer of from 1 to 20, with a hydroxyl group-containing (meth)acrylate, and having, in one molecule, at least two (meth)acryloyl groups and at least two urethane bonds,(B) a radical polymerizable low molecular weight compound, and(C) a photopolymerization initiator.
    Type: Grant
    Filed: June 3, 1986
    Date of Patent: July 14, 1987
    Assignee: Mitsubishi Rayon Company Limited
    Inventors: Hideo Nakamoto, Fumito Aosai, Hiroshi Fukushima, Eriko Suda
  • Patent number: 4666967
    Abstract: The invention provides polyurethanes and polyisocyanurate having incorporated therein a flame retardant amount of a salt formed by reaction between dimethyl methyl phosphonate, monomethyl methyl phosphonate or methyl phosphonic acid, and a compound of the general formula (I). ##STR1## in which X is O, S or NH, R.sup.1 is H, alkyl with 1 to 4 carbon atoms, alkenyl of up to 4 carbon atoms, CN, CONH.sub.2 or NH.sub.2, R.sup.2 is H, alkyl with 1 to 4 carbon atoms or alkenyl of up to 4 carbon atoms or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocyclic ring of up to 6 carbon atoms which may optionally contain another hetero atom and R is H, an alkyl group with 1 to 8 carbon atoms, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 12 carbon atoms or a heterocyclic group with up to 9 ring carbon atoms, or, together with R.sup.1 forms an alkylene chain of 3 to 10 carbon atoms, or R is a group NHR.sup.3 wherein R.sup.
    Type: Grant
    Filed: January 22, 1986
    Date of Patent: May 19, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Norman Richardson, deceased, Brian G. Clubley, Richard J. Dellar
  • Patent number: 4659797
    Abstract: Polyurethane-based matrix materials are made by reacting a phenol which is at least bifunctional with an aromatic isocyanate which is at least difunctional in the presence of 1-40 wt. % soft segment former. The soft segment former is a compound containing long chain aliphatic groups having at least six carbon atoms in the aliphatic group, an isocyanate-reactive group and a molecular weight of from 800 to 10,000. From 90 to 130 equivalent percent of isocyanate groups (based on the total of isocyanate-reactive groups present in the phenol and soft segment former) are employed. These matrix materials are particularly useful in the production of composite materials and as adhesives.
    Type: Grant
    Filed: April 2, 1986
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wulf von Bonin, Johannes Blahak, Ulrich von Gizycki, Lothar Preis
  • Patent number: 4657968
    Abstract: The preparation of a homogeneous solution of a polyol having Formula I or II or mixtures thereof ##STR1## wherein R represents a saturated or unsaturated alkyl group having from 1 to 20 carbon atoms, a saturated or unsaturated alkaryl group having from 7 to 20 carbon atoms, or an aryl group having from 6 to 12 carbon atoms and R' independently represent an alkylene group having from 1 to 4 carbon atoms or an alkylene ether group having from 2 to 50 carbon atoms with an esterol which is a linear oligomeric polyester backbone terminated at one end with a hydroxy group and at the other end with a vinyl group is described.
    Type: Grant
    Filed: May 14, 1986
    Date of Patent: April 14, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4632946
    Abstract: A halogen-free flameproofed thermoplastic molding material consists of a halogen-free thermoplastic resin (A) and one or more further halogen-free components.The thermoplastic resin (A) is present in an amount of from 30 to 90% by weight, based on the molding material. The latter contains, as further components, from 1 to 50% by weight of a phenol/aldehyde resin (B), from 1 to 50% by weight of a nitrogen-containing organic compound (C) and from 3 to 50% by weight of a phosphorus-containing organic compound (D), the percentages in each case being based on the molding material.The molding material is used for the production of flameproofed moldings.
    Type: Grant
    Filed: January 18, 1985
    Date of Patent: December 30, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Muench, Juergen Hambrecht, Adolf Echte, Karl H. Illers, Johann Swoboda
  • Patent number: 4622361
    Abstract: A high modulus polyurethane elastomer having improved combustion resistance and satisfactory physical properties comprising the reaction product of a polyol or polymer polyol, a low molecular weight chain extender, a liquid organic polymeric isocyanate having an average functionality of at least about 2.4 and a defined concentration of flame retardant.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: November 11, 1986
    Assignee: Union Carbide Corporation
    Inventors: William A. Gill, Richard M. Gerkin
  • Patent number: 4608407
    Abstract: The present invention is directed to a process for the production of compression-molded materials by the compression molding lignocellulose-containing materials mixed and/or impregnated with polyisocyanates as binder in the presence of catalysts, the improvement wherein the catalysts used are latent, heat-activatable catalysts based on ammonium salts of the type which can be obtained by reacting(i) monofunctional or polyfunctional, primary, secondary and/or tertiary amines with(ii) alkyl esters of acids of phosphorus.or secondary and/or tertiary amines (i) withacidic alkylester of acids of phosporous (ii) under neutralization in substantially equivalent quantities.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: August 26, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dimitrios Kerimis, Hanns P. Muller, Manfred Kapps
  • Patent number: 4607063
    Abstract: The invention is phosphono-s-triazines corresponding to the formula ##STR1## wherein: X is separately in each occurrence chlorine, bromine, haloalkyl or alkyl;Y is separately in each occurrence hydrogen, chlorine or bromine;R is separately in each occurrence hydrogen, hydrocarbyl, CH.sub.2 Y, CH.sub.2 OH or CH.sub.2 OC(R.sup.1).sub.3 wherein R.sup.1 is alkyl;a is an integer from 0 to 2 inclusive; andb is an integer from 1 to 3 inclusive, with the proviso that the sum of a and b equal 3, and with the further proviso that at least one R is CH.sub.2 OH or CH.sub.2 OC(R.sup.1).sub.3.
    Type: Grant
    Filed: August 9, 1985
    Date of Patent: August 19, 1986
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Sally P. Ginter
  • Patent number: 4594364
    Abstract: The invention is phosphorus compounds containing .alpha.-halo hydroxyalkyl or .alpha.-halo t-alkoxyalkyl groups corresponding to the formula ##STR1## wherein R independently in each occurrence is alkylene, haloalkylene, alkenylene, haloalkenylene, phenylene, diphenylene, halophenylene, dihalophenylene, and oxyalkylene;R.sup.1 independently in each occurrence is hydrogen, CH.sub.2 OR.sup.3, CH.sub.2 OH, haloalkyl, phenyl, halophenyl or methyl phenoxy;R.sup.2 independently in each occurrence is haloalkyl, phenyl, haloaryl or alkyl;R.sup.3 independently in each occurrence is t-alkyl;X independently in each occurrence is bromine or chlorine;a is independently in each occurrence 1 or 2; andb is independently in each occurrence 0 or 1,with the proviso that at least one R.sup.1 is CH.sub.2 OR.sup.3 or CH.sub.2 OH.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Sally P. Ginter
  • Patent number: 4565833
    Abstract: A fire retardant composition for rigid polyurethanes or polyisocyanurates comprises dimethyl methyl phosphonate, diethyl ethyl phosphonate or a mixture thereof and a triaryl phosphate, a trialkyl phosphate or an alkyl/aryl phosphate in a ratio by weight of 5:95 to 95:5. The composition may also contain a halogen-containing flame retardant compound.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: January 21, 1986
    Assignee: Ciba-Geigy AG
    Inventors: David L. Buszard, Richard J. Dellar
  • Patent number: 4555562
    Abstract: A polyurethane elastomer product formed by curing a mixture of an NCO terminated urethane prepolymer and a polyhydroxyalkylphosphine oxide. The polyhydroxyalkyl phosphine curative is a compound of the class having the formula: ##STR1## wherein R is alkylene of 3 to 6 carbon atoms, R.sub.1 is alkyl of 2 to 10 carbon atoms, cycloalkyl of 6 to 12 carbon atoms and n is an integer of 2 to 3. Exemplary polyhydroxyalkyl phosphine curatives are (HOCH.sub.2 CH.sub.2 CH.sub.2).sub.2 P(O)--C.sub.4 H.sub.9 --sec. and (HOCH.sub.2 CH.sub.2 CH.sub.2).sub.3 P(O).
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: November 26, 1985
    Assignee: FMC Corporation
    Inventors: Fui-Tseng H. Lee, Joseph Green
  • Patent number: 4524166
    Abstract: Primary or secondary amino substituted hindered phosphites of the formula ##STR1## are prepared by reaction of the appropriate phosphorus and phenol compounds, said hindered phosphites being useful as stabilizers of organic polymers and lubricating oils.
    Type: Grant
    Filed: September 14, 1984
    Date of Patent: June 18, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor
  • Patent number: 4419299
    Abstract: Phosphonopolyester oligomers are prepared from hydroxyalkylated 2,2',-bis(3-allylphenyl-4-hydroxy) alkanes and phosphonyl dihalides. The oligomers are useful in the preparation of polyester resins, epoxy resins, and polyurethanes.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: December 6, 1983
    Assignee: The Dow Chemical Co.
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4407981
    Abstract: A composition comprises polyurethane, a two-component flame retardant system consisting of an additive first flame retardant containing organophosphorus, and a second flame retardant containing organochlorine or organobromine.The composition of the invention may be employed for polyurethane foams, especially rigid foams.Diminished combustibility for rigid foam is measured by a flame-spread index less than 75 and a smoke developed index less than 450 when subjected to ASTM Test E-84, Surface Burning Characteristics of Building Materials.Dimethyl methylphosphonate is a representative additive organophosphorus first flame retardant. Trichloroisopropyl alcohol is a representative second flame retardant containing organochlorine.
    Type: Grant
    Filed: February 16, 1982
    Date of Patent: October 4, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Alan M. Aaronson
  • Patent number: 4408033
    Abstract: Phosphonopolyester oligomers are prepared from hydroxyalkylated 2,2',-bis(3-allylphenyl-4-hydroxy) alkanes and phosphonyl dihalides. The oligomers are useful in the preparation of polyester resins, epoxy resins, and polyurethanes.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: October 4, 1983
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4380593
    Abstract: Optionally-foamed intumescent compositions obtained by reacting(a) polyisocyanates with(b) phosphorus-containing condensation products having at least 2 hydroxyl groups and obtained by condensing primary or secondary monoamines and/or polyamines optionally containing OH-groups, carbonyl compounds and dialkyl phosphites, optionally followed by alkoxylation, and(c) more than bifunctional polyethers having an average OH-number of from 150 to 500 which have been obtained by the addition of alkylene oxides, of which from 50 to 100% by weight consist of ethylene oxide, with low molecular weight starters, and(d) cyanuric acid and/or cyanuric acid derivatives, and(e) optionally water and(f) optionally other organic compounds containing isocyanate-reactive hydrogen atoms,are used, for example, as cavity-filling, gap-sealing or coating materials.
    Type: Grant
    Filed: February 24, 1982
    Date of Patent: April 19, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wulf von Bonin, Gottfried Zaby
  • Patent number: 4367295
    Abstract: The present invention relates to intumescent compositions, which may be foamed, and which are obtained by reacting:(1) polyisocyanates with(2) phosphorus-containing condensation products having at least one hydroxyl group obtainable by condensing (i) primary or secondary aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic monoamines and/or polyamines, which mono- or polyamines may contain OH-groups; (ii) carbonyl compounds; and, (iii) dialkyl phosphites, and(3) polyesters containing hydroxyl groups and having OH-numbers of from 140 to 300, obtained by reacting polycarboxylic acids containing from 2 to 10 carbon atoms with at least 2 polyols selected from two different groups of the following three:(a) hydroxyl compounds containing more than three OH groups and having molecular weights of up to 200,(b) hydroxyl compounds containing three OH groups and having molecular weights of up to 150,(c) hydroxyl compounds containing two OH-groups and having molecular weights of up to 80, with the proviso tha
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: January 4, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wulf von Bonin
  • Patent number: 4361692
    Abstract: The use of an organic phosphorus acid compound to extend the pot life of urethane reaction mixtures is disclosed.
    Type: Grant
    Filed: September 23, 1981
    Date of Patent: November 30, 1982
    Assignee: PPG Industries, Inc.
    Inventor: Vernon G. Ammons
  • Patent number: 4351915
    Abstract: 2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers which are useful as stabilizers for organic polymeric materials, and have the general formula are disclosed: ##STR1## wherein: Y.sub.1 is ##STR2## A.sub.1, A.sub.2, A.sub.3, A.sub.4, A.sub.5, and A.sub.6 are groups which are defined in the specification, at least one pair of A.sub.1 and A.sub.2 ; A.sub.3 and A.sub.4 ; and A.sub.5 and A.sub.6 being taken together to form the group ##STR3## the groups R.sub.1, R.sub.2, R.sub.3 and Z as well as X, p, and m being as defined in the specification.
    Type: Grant
    Filed: May 26, 1981
    Date of Patent: September 28, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Naohiro Kubota, Toshihiro Shibata, Kazuo Sugibuchi, Motonubu Minagawa
  • Patent number: 4348511
    Abstract: Novel crosslinked unsaturated polymers, which have better properties than conventional crosslinked unsaturated polymers are obtained by reacting a .beta.-aminocrotonic acid ester, .beta.-aminocrotononitrile or .beta.-aminocrotonamide with a diisocyanate or polyisocyanate and a polyol, for example at temperatures of between 50.degree. and 180.degree. C.
    Type: Grant
    Filed: April 30, 1981
    Date of Patent: September 7, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Theobald Haug
  • Patent number: 4343914
    Abstract: Polyurethane compositions are rendered fire retardant by substitution for some of the polyol normally present in the reaction mixture, an effective amount of a 3-hydroxypropyl phosphine oxide such as sec-butyl bis(3-hydroxypropyl) phosphine oxide.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: August 10, 1982
    Assignee: FMC Corporation
    Inventor: Fui-Tseng H. Lee
  • Patent number: 4338412
    Abstract: The present invention is directed to intumescent compositions, which may be foamed, obtained by reacting:(1) polyisocyanates,(2) phosphorus-containing condensation products having at least one hydroxyl group and obtained by condensing (i) primary or secondary aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic monoamines and/or polyamines, which mono- and polyamines may contain OH groups, (ii) carbonyl compounds, and (iii) dialkyl phosphites,(3) aromatic hydroxy carboxylic acids or salts thereof, and(4) optionally, water and/or additional organic compounds containing isocyanate-reactive hydrogen atoms.
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: July 6, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wulf von Bonin
  • Patent number: 4316006
    Abstract: Phosphorus containing polymers are prepared by copolymerizing a cyclic phosphite and an epoxide in the presence of an acid catalyst. The resulting polymer can be incorporated within a thermoplastic or thermosettable resin to increase the flame resistivity thereof.
    Type: Grant
    Filed: February 27, 1980
    Date of Patent: February 16, 1982
    Assignee: The Dow Chemical Company
    Inventor: Gerald K. McEwen
  • Patent number: 4298709
    Abstract: Polyhydroxyl polyether compounds containing at least one monomeric unit each of the formulae: ##STR1## are disclosed. Polymeric condensation resins are prepared by allowing the polyhydroxyl polyethers to react with polyfunctional chain-forming compounds containing functional groups reactive with the hydroxyl groups of polyhydroxyl polyethers. The polyhydroxyl polyether compounds enhance the flame-retardant properties of polymeric condensation resins such as polyurethanes.
    Type: Grant
    Filed: June 25, 1980
    Date of Patent: November 3, 1981
    Assignee: The Dow Chemical Company
    Inventors: Sally P. Ginter, Chester E. Pawloski, Violete L. Stevens
  • Patent number: 4298707
    Abstract: Polymers of anionically polymerized monomers such as mono-olefins, conjugated dienes, vinyl substituted aromatics, vinyl substituted pyridine, vinyl substituted quinolines, various aldehydes, various epoxides, various oxetanes, various oxygen-containing compounds, and the like are produced and end capped with a polyisocyanate or polyisothiocyanate having the formula R--N.dbd.C.dbd.X).sub.n wherein R is a hydrocarbon, n is 2 or 3, and X is oxygen or sulfur. Such end capped polymers, of course, contain one reacted or connected isocyanate or isothiocyanate group and at least one free isocyanate or isothiocyanate end group, which free end group(s) reacts with an amide to give an imide end group. The imide terminated polymer is then hydrolyzed to form a stable amine terminated polymer. The reaction of the amide compound with the isocyanate(s) or isothyiocyanate(s), followed by hydrolysis, results in the replacement of the free isocyanate or isothiocyanate end group(s) with an amine group(s).
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: November 3, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, Richard A. Schwarz, Richard J. Ambrose, Robert A. Hayes
  • Patent number: 4293679
    Abstract: This invention relates to control of particle size of solid, discrete, hydrophilic, crosslinked polyurethane particles formed from a composition which comprises(a) a water reactant;(b) a prepolymer comprising at least one isocyanate-capped polyol having a reaction functionality of at least two, the total of said polyol present having an ethylene oxide content of at least 40 weight percent before capping;(c) a water-soluble solvent for (b) and(d) when the reaction functionality of (b) is two, a crosslinking agent containing at least three functional groups, the volume ratio of (a):(b) being at least 2:1.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: October 6, 1981
    Assignee: W. R. Grace & Co.
    Inventor: Joseph A. Cogliano
  • Patent number: 4288562
    Abstract: The reaction of isocyanates with substances containing isocyanate groups or active hydrogen groups, such as hydroxyl groups, amino groups and the like, are initiated by sulfonium zwitterions such as the ar-cyclic sulfonium areneoxides. Accordingly, partially trimerized isocyanates, polyurethanes and other useful materials can be made.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: September 8, 1981
    Assignee: The Dow Chemical Co.
    Inventors: Jiri Kresta, Chen S. Shen
  • Patent number: 4281097
    Abstract: Novel esters of pentavalent phosphorus acid having the formula ##STR1## wherein R and R'are haloalkyl containing from 2 to 6 carbon atoms and from 1 to 6 halogen atoms; n is an integer of from 1 to 3; each X is independently selected from hydrogen, halogen, alkyl, or hydroxyl, provided that at least one X is hydroxyl. The above compounds are effective reactive flame retardants in polyurethane and polyester polymeric compositions.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: July 28, 1981
    Assignee: Velsicol Chemical Corporation
    Inventor: James A. Albright
  • Patent number: 4280951
    Abstract: Phosphorus-containing condensation products are obtained by effecting condensation between an organophosphorus compound of the Formula, ##STR1## wherein X, Y and Z each is hydrogen or halogen, R.sub.1 and R.sub.2 each is hydrogen or methyl and R.sub.3 is hydrogen or an alkyl group and polyhydric alcohols having at least three alcoholic hydroxyl groups.These condensation products are ueful as a flame retardant for various synthetic resins.
    Type: Grant
    Filed: June 23, 1980
    Date of Patent: July 28, 1981
    Assignee: Sanko Kaihatsu Kagaku Kenkyusho
    Inventors: Toranosuke Saito, Hiroyuki Ohishi
  • Patent number: 4272619
    Abstract: The present invention relates to a process for the production of modified polyether polyols by the radical polymerization of a mixture of acrylonitrile, styrene, a salt of an .alpha.,.beta.-unsaturated monocarboxylic or polycarboxylic acid containing a primary, secondary or tertiary monoamine or polyamine and optionally copolymerizable compounds with a polyether polyol.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: June 9, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Balle, Hansjurgen Rabe, Peter Vehlewald
  • Patent number: 4268633
    Abstract: Phosphorus containing flame retardants are prepared by a two step process having as essential steps:(1) reacting diorgano organophosphonate with reactant comprising phosphorus oxide reagent to yield a metaphosphate/phosphonate reaction product, and thereafter;(2) reacting the reaction product of step (1) with reactant comprising epoxide to yield poly (oxyorganophosphate/phosphonate) product.Selected poly (oxyorganophosphate/phosphonate) products contain a backbone structure of repeating units represented by the average formula: ##STR1## wherein m is an integer from 1 to 50; R, R.sub.1, and R.sub.2 are individually selected from saturated hydrocarbon radical, alkaryl radical, aralkyl radical, and aryl radical; and R.sub.3 is: ##STR2## wherein R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are individually selected from hydrogen atom, hydrocarbon radical, and halogenated hydrocarbon radical.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: May 19, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Ralph B. Fearing
  • Patent number: 4259472
    Abstract: Two component compositions particularly useful as high solids thermosetting coating compositions and molding compositions. Compositions comprise a first component comprising an oligomeric hydroxy functional phosphate ester prepared by reaction of a polyepoxide and an acid phosphate ester; and a second component comprising a isocyanate crosslinking agent.
    Type: Grant
    Filed: January 4, 1980
    Date of Patent: March 31, 1981
    Assignee: Ford Motor Company
    Inventors: Mohinder S. Chattha, Henk Van Oene
  • Patent number: 4257996
    Abstract: The use of polyisocyanates as binders in the preparation of particle boards is subject to the drawback that the boards exhibit a tendency to adhere to the face of the platens used in their formation. This problem is minimized by utilizing, in association with the polyisocyanate to be used as binder, minor amounts of one or more phosphates or thiophosphates of the formula: ##STR1## where R=alkyl (C.sub.3 and higher), alkenyl (C.sub.3 and higher), aryl, alkyl-substituted aryl, ##STR2## (where R.sub.2 is alkyl, aryl, or alkyl-substituted aryl, A and B are H, methyl, chloromethyl, 2,2,2-trichloromethyl, m=1-25) and lower-alkyl substituted by from 1 to 2 acyloxy groups where acyl is the residue of an aliphatic carboxylic acid having at least 2 carbon atoms; R.sub.1 is Cl, Br, lower-alkoxy, lower-alkylmercapto, arylamino, mono(lower-alkyl)amino, di(lower-alkyl)amino, hydroxy(lower-alkylene)oxy, aryloxy, hydrocarbylureido, and an enol residue; X=O or S and n=1 or 2.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: William J. Farrissey, Jr., Alexander McLaughlin, Reinhard H. Richter, Curtis P. Smith, Benjamin W. Tucker
  • Patent number: 4257995
    Abstract: The use of polyisocyanates as binders in the preparation of particle boards is subject to the drawback that the boards exhibit a tendency to adhere to the face of the platens used in their formation. This problem is minimized by incorporating minor amounts of a mixture of certain mono- and di- (saturated or unsaturated aliphatic) acid phosphates or the corresponding pyrophosphates, into the polyisocyanate to be used as binder. The polyisocyanates and the acid phosphates and or pyrophosphates, are applied to the particles separately, or after preblending one with the other. Whether the components are applied separately or in combination one with the other, they can each be applied either neat or in the form of an emulsion or emulsions.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: Alexander McLaughlin, Reinhard H. Richter, Harold E. Reymore, Jr.
  • Patent number: 4258169
    Abstract: A process is disclosed for the preparation of liquid, storage-stable, polyisocyanate compositions containing a release agent formed in situ which compositions are useful, for example, as binder resins in the formation of particle boards which latter, because of the presence of the release agent, show no tendency to adhere to the face of metal platens used in their formation. The process comprises heating an organic polyisocyanate (polymethylene polyphenyl polyisocyanate preferred) with an acid phosphate (e.g. a mixture of mono- and di-alkyl acid phosphates) under conditions controlled as to time and temperature so as to yield a product which is storage stable and shows no tendency to deposit solid or to separate into two liquid phases.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: Richard A. Prather, David L. Williams, Robert M. Partin, Warren J. Rabourn
  • Patent number: 4246206
    Abstract: The invention relates to a process for the preparation of N,N-bis-(2-hydroxyalkyl)-aminomethane phosphonic acid dimethyl esters corresponding to the following general formula: ##STR1## wherein each R, may be the same or different and represents hydrogen or, preferably, a lower, linear or branched alkyl radical or halogen-substituted alkyl radical containing from 1 to 6 carbon atoms.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: January 20, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Heinz Mitschke, Manfred Kapps
  • Patent number: 4220728
    Abstract: The reaction of isocyanates with substances containing isocyanate groups or active hydrogen groups, such as hydroxyl groups, amino groups and the like, are initiated by sulfonium zwitterions such as the ar-cyclic sulfonium areneoxides. Accordingly, partially trimerized isocyanates, polyurethanes and other useful materials can be made.
    Type: Grant
    Filed: March 27, 1978
    Date of Patent: September 2, 1980
    Assignee: The Dow Chemical Company
    Inventors: Jiri Kresta, Chen S. Shen
  • Patent number: 4202946
    Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethylphosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorus-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: May 13, 1980
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, Henri Ulrich
  • Patent number: 4200594
    Abstract: This invention concerns the preparation of dinitrile phosphonates, as well as their hydrolysis into the corresponding diacids, and reduction into the corresponding diamines. These compounds can be used, in particular, to make polyamides, polyurethanes or polyurates fireproof, as well as to increase their adhesive properties.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: April 29, 1980
    Inventors: Georges Sturtz, Jean-Claude Clement
  • Patent number: 4194981
    Abstract: A polyurethane polymer which is the reaction product of a diisocyanate and a particular polyol adduct is described. The polyurethane polymer is a low molecular weight polyurethane polymer particularly useful as a dispersant in lubricating oils. Disclosed herein is an improvement in the dispersancy of certain polyol lubricant dispersants by conversion of the polyol into a polyurethane.
    Type: Grant
    Filed: December 28, 1978
    Date of Patent: March 25, 1980
    Assignee: Texaco Inc.
    Inventors: Kenneth G. Hammond, Raymond C. Schlicht
  • Patent number: 4192927
    Abstract: The present invention relates to new polyols modified by phosphonoformamidine groups, to a process for the preparation thereof and the use thereof as starting component for the preparation of preferably foamed polyurethane plastics.The process involves (A) reacting diisocyanatocarbodiimides corresponding to the following general formula:OCN--R.sup.2 --N.dbd.C.dbd.N).sub.m R.sup.2 --NCOat a temperature of from about 25 to 130.degree. C., optionally in the presence of an inert solvent, with polyhydroxyl compounds corresponding to the following general formula:A--OH).sub.nin an OH/NCO-ratio of from 1.2:1 to 30:1 to form a polyhydroxyl compound containing carbodiimide groups and (B) completely or partially reacting the carbodiimide groups remaining in the product of step (A) by means of a basic catalyst at a temperature of from 25 to 150.degree. C.
    Type: Grant
    Filed: April 16, 1979
    Date of Patent: March 11, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schafer, Kuno Wagner, Kurt Findeisen
  • Patent number: 4187354
    Abstract: The invention broadly relates to greatly lowering the viscosity of the self-condensation products of formaldehyde (formose) by mixing formose with dialkyl phosphites; trialkyl phosphites and .alpha.-hydroxy- or .alpha.-amino-phosphonic acid esters. These mixtures have the surprising capacity of dissolving large quantities of crystallized sugars. Compounds capable of aminoplast formation may also be advantageously mixed in. These mixtures have the remarkable ability of being used to make flame-resistant, open-celled, highly carbonizing rigid polyurea-polyurethane foams with isocyanate indexes of as low as 45 to 50.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: February 5, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kuno Wagner
  • Patent number: RE31703
    Abstract: A process is disclosed for the preparation of liquid, storage-stable, polyisocyanate compositions containing a release agent formed in situ which compositions are useful, for example, as binder resins in the formation of particle boards which latter, because of the presence of the release agent, show no tendency to adhere to the face of metal platens used in their formation. The process comprises heating an organic polyisocyanate (polymethylene polyphenyl polyisocyanate preferred) with an acid phosphate (e.g. a mixture of mono- and di-alkyl acid phosphates) under conditions controlled as to time and temperature so as to yield a product which is storage stable and shows no tendency to deposit solid or to separate into two liquid phases.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: October 9, 1984
    Assignee: The Upjohn Company
    Inventors: Richard A. Prather, David L. Williams, Robert M. Partin, Warren J. Rabourn, deceased