Phosphorus-containing Reactant Patents (Class 528/287)
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Patent number: 4354019Abstract: An oxidated silicon compound will react with a substituted organic compound in the presence of an alkali compound to produce organic alkali metal silicate products which may be used as molding powders, as adhesives, as coating agents and be reacted with polyisocyanates to produce insulating foams.Type: GrantFiled: December 10, 1981Date of Patent: October 12, 1982Inventor: David H. Blount
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Patent number: 4351915Abstract: 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: GrantFiled: May 26, 1981Date of Patent: September 28, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Naohiro Kubota, Toshihiro Shibata, Kazuo Sugibuchi, Motonubu Minagawa
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Patent number: 4315969Abstract: The present invention provides new linear phosphorus- and halogen-containing flame retardant polyester additives for normally flammable polymers and coatings for normally flammable natural and synthetic films and fibers, for instance, polyester and cellulose ester films and fibers. The phosphorus- and halogen-containing polymers of the invention are water dispersible or can be rendered water-soluble. They can be prepared by reacting a phosphorus acid reactant such as phosphoric acid with at least one halogenated difunctional monomer. The water-soluble polyesters can be cross-linked to render them insoluble in water by heating together with a methylol compound.Said halogenated monomer is preferably an oxyalkylated diacid or diol and said halogen is attached either on one or more aromatic rings or on a cycloaliphatic ring.Type: GrantFiled: July 20, 1979Date of Patent: February 16, 1982Assignee: BASF Wyandotte CorporationInventors: Robert B. Login, David D. Newkirk
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Patent number: 4315847Abstract: The present invention provides new linear phosphorus- and halogen-containing flame retardant polyester additives for normally flammable polymers and coatings for normally flammable natural and synthetic films and fibers, for instance, polyester and cellulose ester films and fibers. The phosphorus- and halogen-containing polymers of the invention are water dispersible or can be rendered water-soluble. They can be prepared by reacting a phosphorus acid reactant such as phosphoric acid with at least one halogenated difunctional monomer. The water-soluble polyesters can be cross-linked to render them insoluble in water by heating together with a methylol compound.Said halogenated monomer is preferably an oxyalkylated diacid or diol and said halogen is attached either on one or more aromatic rings or on a cycloaliphatic ring.Type: GrantFiled: July 20, 1979Date of Patent: February 16, 1982Assignee: BASF Wyandotte CorporationInventors: Robert B. Login, David D. Newkirk
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Patent number: 4314052Abstract: Improved polyesters soluble or dispersible in water having an apparent average molecular weight of 800 to 5,000 and containing phosphonic ester moieties are useful as levelling auxiliaries for uniform dyeing and are produced by esterifying dibasic acids and dihydric alcohols, either or both of which contain phosphonic acid moieties, phosphonic acid ester moieties or both.Type: GrantFiled: January 7, 1980Date of Patent: February 2, 1982Assignee: Cassella AktiengesellschaftInventors: Friedrich Engelhardt, Karl Hintermeier, Joachim Ribka, Walter Dursch, Walter Rupp
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Patent number: 4298709Abstract: 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: GrantFiled: June 25, 1980Date of Patent: November 3, 1981Assignee: The Dow Chemical CompanyInventors: Sally P. Ginter, Chester E. Pawloski, Violete L. Stevens
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Patent number: 4280951Abstract: 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: GrantFiled: June 23, 1980Date of Patent: July 28, 1981Assignee: Sanko Kaihatsu Kagaku KenkyushoInventors: Toranosuke Saito, Hiroyuki Ohishi
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Patent number: 4281097Abstract: 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: GrantFiled: April 23, 1980Date of Patent: July 28, 1981Assignee: Velsicol Chemical CorporationInventor: James A. Albright
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Patent number: 4259222Abstract: The present invention provides new linear phosphorus- and halogen-containing flame retardant polyester additives for normally flammable polymers and coatings for normally flammable natural and synthetic films and fibers, for instance, polyester and cellulose ester films and fibers. The phosphorus- and halogen-containing polymers of the invention are water dispersible or can be rendered water-soluble. They can be prepared by reacting a phosphorus acid reactant such as phosphoric acid with at least one halogenated difunctional monomer. The water-soluble polyesters can be cross-linked to render them insoluble in water by heating together with a methylol compound.Said halogenated monomer is preferably an oxyalkylated diacid or diol and said halogen is attached either on one or more aromatic rings or on a cycloaliphatic ring.Type: GrantFiled: August 16, 1978Date of Patent: March 31, 1981Assignee: BASF Wyandotte CorporationInventors: Robert B. Login, David D. Newkirk
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Patent number: 4254018Abstract: Polyesters containing a freely or chemically incorporated heat stabilizing agent which is a phosphonate of the chemical formula: ##STR1## in which R.sub.1 and R.sub.2 may be identical or different and describe an alkyl radical with 1 to 4 carbon atoms, and in which X represents ##STR2## in amounts representing 10 to 400 ppm phosphorus.Type: GrantFiled: March 1, 1978Date of Patent: March 3, 1981Assignee: Akzona IncorporatedInventors: Jochen Kowallik, Alexander Brandner
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Patent number: 4251402Abstract: There is disclosed a cellulosic material such as paper or paperboard surface-sized with an aqueous dispersion of a combination of degraded starch or a starch derivative and a branched-chain, water-dispersible polyester condensation product. Said polyester is derived from the reaction of a dicarboxylic reactant, a diol or polyoxyalkylene glycol, and a phosphorus acid reactant wherein said polyester has a carboxylic acid number of about 5 to about 15 and an average molecular weight of about 4,000 to about 11,000. Mixtures of said starch and said polyester when used to surface-size cellulosic materials impart water resistance thereto.Type: GrantFiled: July 30, 1979Date of Patent: February 17, 1981Assignee: BASF Wyandotte CorporationInventors: Robert B. Login, Daniel R. Dutton
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Patent number: 4235990Abstract: Carboxy phosphorus acid compounds react by a metathesis reaction in a liquid media with tetravalent metal ions to yield layered crystalline inorganic polymers having the empirical formula M(O.sub.3 PR.sub.n COOH).sub.2 where M is a tetravalent metal and R is an organic group covalently bonded to phosphorous and the terminal carboxy group and n is 0 or 1.Type: GrantFiled: October 17, 1978Date of Patent: November 25, 1980Assignee: Occidental Research CorporationInventors: Peter M. DiGiacomo, Martin B. Dines
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Patent number: 4214069Abstract: Flame-resistant copolyesters are disclosed consisting or consisting essentially of from 85 to 99.5% of repeating units of the formula --CO--R--CO--O--R.sub.1 --O-- in which R is a divalent aromatic radical and R.sub.1 is a divalent aliphatic, cycloalkane radical or a mixture of two or several of these radicals; and least 0.5% of units of the formula: ##STR1## in which Me represents a metal such as Na, K, Ca or Zn, and Z represents a paraphenylene group or a divalent aliphatic grouping which contains from 1 to 18 carbon atoms, and may comprise heteroatoms, and is optionally branched, the branch being an aliphatic radical which may be halogenated, and comprises from 1 to 6 carbon atoms; and from 0 to 14.5% of units produced from a brominated compound of the formula: ##STR2## in which R.sub.5 is zero or represents a grouping: ##STR3## and A and A' represent either --CO--OX groups, where X=H or a lower alkyl group, or --X'OH groups, where X'=a--OCH.sub.2 --CH.sub.2 --.sub.n group, and n=1 to 10.Type: GrantFiled: October 12, 1977Date of Patent: July 22, 1980Assignee: Rhone-Poulenc-TextileInventors: Paul Couchoud, Yves Vaginay
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Patent number: 4210740Abstract: The present invention relates to copolyesters having high flame resistance, and comprising essentially 85% to 99.5% of repeating units of the formula --CO--R--CO--O--R.sub.1 --O--, in which R is an aromatic radical, and R.sub.1 is a divalent aliphatic, cycloaliphatic or cyclanic radical, or a mixture of two or more of these radicals;at least 0.5% of units of the formula: ##STR1## in which R' is a lower alkyl group, and R" is an aliphatic, aromatic or arylaliphatic radical;and 0 to 14.5% of units produced from a compound of the formula: ##STR2## in which R.sub.2 is zero or represents an ##STR3## --CH.sub.2 -- or --O-- group, and A and A' represent either --CO--OX groups, in which X.dbd.H or a lower alkyl group, or --X'0H groups in which X'.dbd.a --(OCH.sub.2 --CH.sub.2 -- group and n=1 to 10.These copolyesters may be used advantageously for producing textile yarns and fibers, films, and molded or extruded articles.Type: GrantFiled: January 30, 1978Date of Patent: July 1, 1980Assignee: Rhone-Poulenc-TextileInventor: Paul Couchoud
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Patent number: 4210685Abstract: There is disclosed a cellulosic material such as paper or paperboard surface-sized with an aqueous dispersion of a combination of degraded starch or a starch derivative and a branched-chain, water-dispersible polyester condensation product. Said polyester is derived from the reaction of a dicarboxylic reactant, a diol or polyoxyalkylene glycol, and a phosphorus acid reactant wherein said polyester has a carboxylic acid number of about 5 to about 15 and an average molecular weight of about 4,000 to about 11,000. Mixtures of said starch and said polyester when used to surface-size cellulosic materials impart water resistance thereto.Type: GrantFiled: May 22, 1978Date of Patent: July 1, 1980Assignee: BASF Wyandotte CorporationInventors: Robert B. Login, Daniel R. Dutton
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Patent number: 4200594Abstract: 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: GrantFiled: December 19, 1977Date of Patent: April 29, 1980Inventors: Georges Sturtz, Jean-Claude Clement
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Patent number: 4191715Abstract: A compound having the formula ##STR1## This compound is useful in enhancing the flame retardancy of polyesters.Type: GrantFiled: July 3, 1978Date of Patent: March 4, 1980Assignee: Monsanto CompanyInventors: Chester C. Wu, Albert Y. Garner
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Patent number: 4180495Abstract: Polyesters, polyamides and polyester-polyamides are flame retarded by incorporating a flame retardant amount of selected poly(metal phosphinate)s with the resins. The poly(metal phosphinate)s can be incorporated with the resins either by admixture of the poly(metal phosphinate)s with the polyester or polyamide or by adding the poly(metal phosphinate)s to the polyester or polyamide polymerization reaction whereby the poly(metal phosphinate)s become a part of the polymer structure.Type: GrantFiled: April 13, 1978Date of Patent: December 25, 1979Assignee: Pennwalt CorporationInventor: Stanley R. Sandler
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Patent number: 4169935Abstract: Disclosed is a biaxially oriented polyester film, wherein the polyester comprises a linear polyester comprising a dicarbocyclic acid and a diol, and further including from about 3 to 20 mole percent of the dicarboxylic acid of a phosphorus-containing chain member having structural units of the formula ##STR1## wherein R is a saturated, open-chain or cyclic alkylene radical, an arylene radical or an aralkylene radical, andR.sub.1 is an alkyl group containing up to 6 carbon atoms, an aryl or an aralkyl group.Also disclosed is the use of this film as an electrical insulator.Type: GrantFiled: June 7, 1978Date of Patent: October 2, 1979Assignee: Hoechst AktiengesellschaftInventors: Klaus Hoheisel, Ulrich Bollert, Siegfried Janocha
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Patent number: 4157436Abstract: The present invention relates to a flame retardant polyester having a phosphorus atom content of 500-50,000 ppm, which polyester contains a flame-retarding amount of a phosphorus containing compound represented by the following general formula: ##STR1## wherein each of R.sup.1 is a hydrogen atom or hydrocarbon group having 1-10 carbon atoms which may contain a hydroxyl group, and both R.sup.1 's may together form a dehydrated ring when both of R.sup.1 's represent hydrogen atoms, each of R.sup.2 and R.sup.3 is a member selected from the group consisting of halogen atoms and hydrocarbon groups having 1-10 carbon atoms, and each of n2 and n3 is an integer of 0-4. Polyesters containing the claimed phosphorus containing compounds are characterized by exhibiting excellent flame retardancy and at the same time, the physical properties of the polyesters are not impaired by incorporation of the phosphorus compound therein.Type: GrantFiled: December 9, 1977Date of Patent: June 5, 1979Assignee: Toyo Boseki Kabushiki KaishaInventors: Seiji Endo, Takao Kashihara, Akitada Osako, Tatsuhiko Shizuki, Tadashi Ikegami
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Patent number: 4145510Abstract: Hydantoins of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 8 carbon atoms, R.sub.2 is ##STR2## R.sub.3 is alkyl of 1 to 8 carbon atoms, and X is a straight or branched chain alkylene of 1 to 4 carbon atoms or a straight or branched chain alkylene of 3 to 6 carbon atoms containing an internal carbamido group; or R.sub.1 and R.sub.2 together are Y where Y is a straight or branched chain alkylene of 4 to 8 carbon atoms having a pendant ##STR3## ARE PREPARED BY REACTING FIRST .alpha.,.beta.-UNSATURATED ALDEHYDES OR KETONES WITH ALKYL PHOSPHITES TO FORM A PHOSPHONATE ALDEHYDE OR KETONE FOLLOWED BY A CLASSICAL Bucherer hydantoin synthesis.Type: GrantFiled: March 9, 1978Date of Patent: March 20, 1979Assignee: Ciba-Geigy CorporationInventors: Luther A. R. Hall, David A. Gordon
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Patent number: 4133846Abstract: 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: GrantFiled: June 30, 1977Date of Patent: January 9, 1979Assignee: Velsicol Chemical CorporationInventor: James A. Albright
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Patent number: 4127565Abstract: A flame-retardant, easily dyeable polyester and the process for preparing the same by polycondensing a glycol phthalate prepolymer with a phosphine oxide and dye improver selected from the group consisting ofR--O(G--O).sub.x --Hwhere R is an alkyl group containing an average of from about 8 to about 20 carbon atoms; G is a hydrocarbon radical selected from the group consisting of ethylene, propylene, butylene and isomers thereof, and mixtures of the above, and x has a value of about 8-20, and ##STR1## where R is O, (CH.sub.3).sub.2 or H.sub.2 and the sum of x and y is 4-30. The polymer will be made up of 82 to 98 weight percent of the prepolymer, 8 to 1 weight percent of the dyeability improver and 10-1 weight percent of the phosphine oxide and is preferably formed in the presence of a catalyst which is the reaction product of germanium dioxide and a tetraalkyl ammonium hydroxide.Type: GrantFiled: December 22, 1977Date of Patent: November 28, 1978Assignee: Monsanto CompanyInventors: Henry L. King, Chester C. Wu
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Patent number: 4127590Abstract: The present invention relates to a phosphorus-containing compound of the formula ##STR1## wherein each of R.sup.1 is a hydrogen atom or hydrocarbon group having 1-10 carbon atoms which may contain a hydroxyl group, and both R.sup.1 's may together form a dehydrated ring when both of R.sup.1 's represent hydrogen atoms, each of R.sup.2 and R.sup.3 is a member selected from the group consisting of halogen atoms and hydrocarbon groups having 1-10 carbon atoms, and each of n2 and n3 is an integer of 0-4. These compounds are especially useful for incorporation into polymers, such as polyesters, as flame-retardants. Further, such phosphorus-containing compound imparts excellent flame-retardant properties to such polyesters, while at the same time does not deleteriously affect the physical properties of the polyester.Type: GrantFiled: October 7, 1976Date of Patent: November 28, 1978Assignee: Toyo Boseki Kabushiki KaishaInventors: Seiji Endo, Takao Kashihara, Akitada Osako, Tatsuhiko Shizuki, Tadashi Ikegami
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Patent number: 4127566Abstract: A process for preparation of flame retardant, fiber-forming polyesters by polycondensing a glycol phthalate and a phosphine oxide in the presence of the reaction product of germanium dioxide and a tetraalkyl ammonium hydroxide.Type: GrantFiled: December 22, 1977Date of Patent: November 28, 1978Assignee: Monsanto CompanyInventors: Henry L. King, Chester C. Wu
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Patent number: 4111816Abstract: There are disclosed a phosphorus-containing polyester and size compositions especially useful for sizing spun and continuous filament yarn produced from hydrophobic fibers and useful in protecting these fibers from abrasion during the weaving process. When the size is used alone or in mixtures with conventional size agents such as starches and polyvinyl alcohol, improved adhesion is obtained to hydrophobic fibers or blends thereof with cotton or other hydrophilic fibers. Polyester, polypropylene and polyamide and other fibers are effectively sized with the size compositions of the invention. The polyester consists of a branched chain phosphorus-containing polymer which is the reaction product of at least one dicarboxylic reactant, at least one diol or polyoxyalkylene glycol and a phosphorus acid reactant selected from the class consisting of phosphorus pentoxide, phosphoric acid and mixtures thereof.Type: GrantFiled: June 27, 1977Date of Patent: September 5, 1978Assignee: BASF Wyandotte CorporationInventor: Robert Bernard Login
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Patent number: 4098741Abstract: There are disclosed a phosphorus-containing polyester and size compositions especially useful for sizing spun and continuous filament yarn produced from hydrophobic fibers and useful in protecting these fibers from abrasion during the weaving process. When the size is used alone or in mixtures with conventional size agents such as starches and polyvinyl alcohol, improved adhesion is obtained to hydrophobic fibers or blends thereof with cotton or other hydrophilic fibers. Polyester, polypropylene and polyamide and other fibers are effectively sized with the size compositions of the invention. The polyester consists of a branched chain phosphorus-containing polymer which is the reaction product of at least one dicarboxylic reactant, at least one diol or polyoxyalkylene glycol and a phosphorus acid reactant selected from the class consisting of phosphorus pentoxide, phosphoric acid and mixtures thereof.Type: GrantFiled: September 30, 1976Date of Patent: July 4, 1978Assignee: BASF Wyandotte CorporationInventor: Robert Bernard Login
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Patent number: RE30783Abstract: Flame-repellant linear polyesters are obtained by incorporating by condensation phosphorus-compounds having the formula ##STR1## wherein R and R.sub.1 are organic radicals which may also contain hereto atoms into the linear polyesters, preferably those from terephthalic acid and ethylene glycol. These polyesters are materials of which flame-repellent filaments, fibers, sheets, press-moulded and injection-moulded articles may be made. Products of the invention can be used whereever especially acute risks of ignition and fire exist.Type: GrantFiled: February 11, 1980Date of Patent: October 27, 1981Assignee: Hoechst AktiengesellschaftInventors: Hans-Jerg Kleiner, Manfred Finke, Ulrich Bollert, Walter Herwig