GB1093893A - Mixtures of phosphonates, their preparation and use in polyurethane foams - Google Patents
Mixtures of phosphonates, their preparation and use in polyurethane foamsInfo
- Publication number
- GB1093893A GB1093893A GB761865A GB761865A GB1093893A GB 1093893 A GB1093893 A GB 1093893A GB 761865 A GB761865 A GB 761865A GB 761865 A GB761865 A GB 761865A GB 1093893 A GB1093893 A GB 1093893A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- mixture
- phosphonates
- aryl
- alkenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/388—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5357—Esters of phosphonic acids cyclic
Abstract
A foamable composition comprises (A) an hydroxyl-containing polymer having an hydroxyl number of from 25 to 900; (B) a mixture of phosphonates falling within at least two of the following classes <FORM:1093893/C3/1> <FORM:1093893/C3/2> <FORM:1093893/C3/3> wherein n is 0 or 1, R3, R4, R5\h and R6 are independently alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl and heterocyclic, R1 is hydrogen or one of the groups listed under R3, R4, R5 and R6, Z i alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkylene or substituted alkylene, and in which the phosphonates of classes (b) and (c) each contain from 2 to 12 free hydroxyl groups and the phosphonates of class (a) contain from 3 to 12 free hydroxyl groups; (c) an organic polyisocyanate; and (d) a foaming agent. The phosphonate mixture may be employed in an amount of 0.2 to about 95% of the polyol component (e.g. a polyester or a polyether or a mixture thereof) contained in a urethane foam system which may also include a blowing agent, a catalyst and a surfactant. The polyol phosphonate may be blended by conventional means with the other components of the urethane foam system at 0-150 DEG C. In Examples 22-26 the hydroxyl-containing polymer employed is derived from trimethylol propane and adipic and the isocyanate employed is a toluene diisocyanate. In Example 27, triphenyl phosphite and isobutanol are reacted at 120-130 DEG C. in the presence of a minor amount of sodium hydride, subsequently with an oxypropylated Novolak (mol. weight 425 and off number 396) at 130-140 DEG C. and the resulting reaction mixture was isomerized by adding epichlorhydrin followed by heating at 140-150 DEG C. The product is identified as oxypropylated Novolak isobutyl epichlorhydrin phosphonate and oxypropylated Novolak isobutyl phosphonate.ALSO:The invention comprises a mixture of phosphonates falling within at least two of the following classes: <FORM:1093893/C2/1> <FORM:1093893/C2/2> <FORM:1093893/C2/3> wherein n is 0 or 1, R3, R4, R5 and R6 are independently alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl and heterocyclic, R1 is hydrogen or one of the groups listed under R3, R4, R5 and R6, Z is alkyl substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkylene or substituted alkylene, and in which the phosphonates of classes (b) and (c) each contain from 2 to 12 free hydroxyl groups and the phosphonates of class (a) contain from 3 to 12 free hydroxyl groups. The invention also includes a process for preparing a mixture of phosphonates which comprises reacting one mole of a triorgano phosphite with more than one mole, but less than three moles, of a polyhydric compound of the formula R7(OH)m in which R7 is alkylene, aralkylene, haloalkyl, aryl, alkaryl, haloaryl, alkenylene, substituted alkenylene, heterocyclic and substituted heterocyclic and m is an integer from 2 to 12, to form a mixture of phosphites, and rearranging the mixture of phosphites to form a corresponding mixture of phosphonates. The transesterification of the triorgano phosphite with the polyhydric compound is preferably effected in the presence of a conventional transesterification catalyst and the rearrangement of the phosphite to form the phosphonate may be effected by heating or by treatment with an Arbujov reagent (many being specified); the nature of the products may apparently be varied by varying the amount of Arbujov reagent employed. The reactions of the invention may be effected at temperatures of 25-300 DEG C. and the reaction may be conducted in situ without the removal of by-products until the desired phosphonate mixture is obtained.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34825264A | 1964-02-28 | 1964-02-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1093893A true GB1093893A (en) | 1967-12-06 |
Family
ID=23367226
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB761865A Expired GB1093893A (en) | 1964-02-28 | 1965-02-22 | Mixtures of phosphonates, their preparation and use in polyurethane foams |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE678414A (en) |
DE (1) | DE1570738A1 (en) |
FR (1) | FR1431188A (en) |
GB (1) | GB1093893A (en) |
NL (1) | NL6502541A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103180331A (en) * | 2010-09-23 | 2013-06-26 | Icl-Ip美国公司 | Monohydroxy cyclic phosphonate substantially free of polyhydoxy phosphonate, process for making same and flame retardant flexible polyurethane foam obtained therefrom |
-
1965
- 1965-02-22 GB GB761865A patent/GB1093893A/en not_active Expired
- 1965-02-26 DE DE1965H0055324 patent/DE1570738A1/en active Pending
- 1965-03-01 FR FR7431A patent/FR1431188A/en not_active Expired
- 1965-03-01 NL NL6502541A patent/NL6502541A/xx unknown
-
1966
- 1966-03-24 BE BE678414D patent/BE678414A/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103180331A (en) * | 2010-09-23 | 2013-06-26 | Icl-Ip美国公司 | Monohydroxy cyclic phosphonate substantially free of polyhydoxy phosphonate, process for making same and flame retardant flexible polyurethane foam obtained therefrom |
US8921439B2 (en) | 2010-09-23 | 2014-12-30 | Icl-Ip America Inc. | Monohydroxy cyclic phosphonate substantially free of polyhydroxy phosphonate, process for making same and flame retardant flexible polyurethane foam obtained therefrom |
Also Published As
Publication number | Publication date |
---|---|
DE1570738A1 (en) | 1970-03-12 |
BE678414A (en) | 1966-09-01 |
FR1431188A (en) | 1966-03-11 |
NL6502541A (en) | 1965-08-30 |
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