GB1390655A - Preparation of flame-retardant organo-phosphorus compounds and flame-retardant polymer compositions containing them - Google Patents
Preparation of flame-retardant organo-phosphorus compounds and flame-retardant polymer compositions containing themInfo
- Publication number
- GB1390655A GB1390655A GB4941872A GB4941872A GB1390655A GB 1390655 A GB1390655 A GB 1390655A GB 4941872 A GB4941872 A GB 4941872A GB 4941872 A GB4941872 A GB 4941872A GB 1390655 A GB1390655 A GB 1390655A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphine oxide
- tris
- flame
- retardant
- oxide
- 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
- 239000003063 flame retardant Substances 0.000 title abstract 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title abstract 3
- -1 flame-retardant organo-phosphorus compounds Chemical class 0.000 title abstract 3
- 229920000642 polymer Polymers 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title 1
- 239000007983 Tris buffer Substances 0.000 abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 abstract 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 abstract 2
- WCWJDBLSRZWRFC-UHFFFAOYSA-N 1-[methyl-(3-nitrophenyl)phosphoryl]-3-nitrobenzene Chemical compound C=1C=CC([N+]([O-])=O)=CC=1P(=O)(C)C1=CC=CC([N+]([O-])=O)=C1 WCWJDBLSRZWRFC-UHFFFAOYSA-N 0.000 abstract 1
- HMNREAWUEAFPIB-UHFFFAOYSA-N 3-bis(3-hydroxyphenyl)phosphorylphenol Chemical compound OC1=CC=CC(P(=O)(C=2C=C(O)C=CC=2)C=2C=C(O)C=CC=2)=C1 HMNREAWUEAFPIB-UHFFFAOYSA-N 0.000 abstract 1
- ORYPIJUZQKZQAF-UHFFFAOYSA-N 5-bis(5-amino-2,4-dibromophenyl)phosphoryl-2,4-dibromoaniline Chemical compound BrC1=C(C=C(C(=C1)Br)N)P(C1=C(C=C(C(=C1)N)Br)Br)(C1=C(C=C(C(=C1)N)Br)Br)=O ORYPIJUZQKZQAF-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- PEGCITODQASXKH-UHFFFAOYSA-N [methyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C)C1=CC=CC=C1 PEGCITODQASXKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 1
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 Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08K5/5397—Phosphine oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
1390655 Halogen-containing phosphine oxides M & T CHEMICALS Inc 26 Oct 1972 [12 Nov 1971] 49418/72 Heading C2P [Also in Division C3] Tertiary phosphine oxides or sulphides of the general formula wherein Ar which may contain an inert substituent is a chlorinated or brominated arylene hydrocarbon radical containing up to 12 carbon atoms, R<SP>1</SP> which may contain an inert substituent is selected from ArYH and alkyl, cycloalkyl, aryl, alkaryl or aralkyl radicals containing up to 12 carbon atoms, Y is -NH- or -O- and Z is O or S are obtained by reacting chlorine or bromine with a corresponding phosphine oxide or sulphide containing at least two amino- or hydroxyl substituted aromatic radicals. From 1 to 3 atoms of Br or Cl is suitably introduced into each Ar radical. The products are useful as flame-retardant additives to polymers or may be reacted with various polyfunctional compounds to give flame retardant polymers. Tris (m-nitrophenyl) phospine oxide is obtained by nitrating triphenyl phosphine oxide with HNO 3 /H 2 SO 4 and is converted to tris (maminophenyl)phosphine oxide by treatment with SnC1 2 /HC1. The product is then brominated to form tris(2,4-dibromo-5-aminophenyl) phosphine oxide. Tris (m-hydroxyphenyl) phosphine oxide is obtained by treating the corresponding tris (m-aminophenyl) compound dissolved in aqueous H 2 SO 4 with an aqueous solution of NaNO 2 and then hydrolysing. Methyl diphenyl phosphine oxide is obtained by reacting methyl magnesium chloride with triphenyl phosphine oxide in tetrahydrofuran and is converted to methyl bis (m-nitrophenyl) phosphine oxide by nitration with HNO 3 /H 2 SO 4 .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19840571A | 1971-11-12 | 1971-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390655A true GB1390655A (en) | 1975-04-16 |
Family
ID=22733242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4941872A Expired GB1390655A (en) | 1971-11-12 | 1972-10-26 | Preparation of flame-retardant organo-phosphorus compounds and flame-retardant polymer compositions containing them |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4859144A (en) |
| DE (1) | DE2254902A1 (en) |
| FR (1) | FR2160159A1 (en) |
| GB (1) | GB1390655A (en) |
| NL (1) | NL7215271A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2459491A1 (en) * | 1974-12-17 | 1976-06-24 | Bayer Ag | AGAINST ISOCYANATE-REACTIVE PHOSPHORUS FLAME RETARDANTS |
| JPH0327850Y2 (en) * | 1984-12-21 | 1991-06-17 | ||
| EP1363922B1 (en) | 2001-02-15 | 2006-07-26 | Great Lakes Chemical Corporation | Novel hydroxyaryl phosphine oxides mixture, glycidyl ethers and epoxy compositions, composites and laminates derived therefrom |
| US6887950B2 (en) | 2001-02-15 | 2005-05-03 | Pabu Services, Inc. | Phosphine oxide hydroxyaryl mixtures with novolac resins for co-curing epoxy resins |
-
1972
- 1972-10-26 GB GB4941872A patent/GB1390655A/en not_active Expired
- 1972-11-09 DE DE19722254902 patent/DE2254902A1/en active Pending
- 1972-11-10 FR FR7239873A patent/FR2160159A1/fr not_active Withdrawn
- 1972-11-10 NL NL7215271A patent/NL7215271A/xx not_active Application Discontinuation
- 1972-11-13 JP JP11303872A patent/JPS4859144A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4859144A (en) | 1973-08-18 |
| FR2160159A1 (en) | 1973-06-22 |
| NL7215271A (en) | 1973-05-15 |
| DE2254902A1 (en) | 1973-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |