DE19621880A1 - Halogen-free cyclic phosphate ester(s) useful as flame retardants - Google Patents
Halogen-free cyclic phosphate ester(s) useful as flame retardantsInfo
- Publication number
- DE19621880A1 DE19621880A1 DE1996121880 DE19621880A DE19621880A1 DE 19621880 A1 DE19621880 A1 DE 19621880A1 DE 1996121880 DE1996121880 DE 1996121880 DE 19621880 A DE19621880 A DE 19621880A DE 19621880 A1 DE19621880 A1 DE 19621880A1
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- phosphoric acid
- dimethylphenyl
- dimethyl
- free cyclic
- 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.)
- Withdrawn
Links
- -1 cyclic phosphate ester Chemical class 0.000 title claims abstract description 22
- 239000003063 flame retardant Substances 0.000 title claims description 3
- 229910019142 PO4 Inorganic materials 0.000 title abstract 2
- 239000010452 phosphate Substances 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 16
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012442 inert solvent Substances 0.000 claims abstract description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- VZMUCIBBVMLEKC-UHFFFAOYSA-N 2-chloro-5,5-dimethyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(Cl)(=O)OC1 VZMUCIBBVMLEKC-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- 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
- C07F9/547—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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Description
Die Erfindung betrifft halogenfreie cyclische Phosphorsäureester, ein Verfahren zu ihrer Herstellung und ihre Verwendung.The invention relates to halogen-free cyclic phosphoric acid esters, a process for their Manufacture and its use.
Einige cyclische Phosphorsäureester sind bereits in der Literatur beschrieben. So findet sich im Chemical Abstracts 93, 133 266 (1980) ein Hinweis auf verschiedene Halogenalkylester von cyclischen Phosphorsäureestern. Ferner wurden von R.M. Mc Connell und H.W. Cooverjr. [J. Org. Chem 24, 630-635 (1959)] weitere cyclische Phosphorsäureester syn thetisiert und charakterisiert.Some cyclic phosphoric acid esters have already been described in the literature. So it is found in Chemical Abstracts 93, 133 266 (1980) a reference to various haloalkyl esters of cyclic phosphoric acid esters. R.M. Mc Connell and H.W. Cooverjr. [J. Org. Chem 24, 630-635 (1959)] further cyclic phosphoric acid esters syn thetized and characterized.
Überraschenderweise konnte nun eine Reihe neuer halogenfreier cyclischer Phosphorsäu reester synthetisiert und analytisch charakterisiert werden.Surprisingly, a number of new halogen-free cyclic phosphoric acid could now reester synthesized and characterized analytically.
Die vorliegende Erfindung betrifft daher neue halogenfreie cyclische Phosphorsäureester der allgemeinen Formel (I)The present invention therefore relates to new halogen-free cyclic phosphoric acid esters of the general formula (I)
mit
R = 2-Methylphenyl, 3-Methylphenyl, 4-Methylphenyl, 2,3-Dimethylphenyl,
2,4-Dimethylphenyl, 2,5-Dimethylphenyl oder 3,4-Dimethylphenyl.
With
R = 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl or 3,4-dimethylphenyl.
Die Erfindung betrifft ebenfalls ein Verfahren zur Herstellung der vorgenannten cyclischen Phosphorsäureester, bei dem man in einem 1. Reaktionsschritt 2,2-Dimethyl-1,3-propandiol mit Phosphoroxichlorid zum cyclischen Phosphorsäureesterchlorid (II) umsetzt:The invention also relates to a method for producing the aforementioned cyclic Phosphoric acid ester, in which in a 1st reaction step 2,2-dimethyl-1,3-propanediol reacted with phosphorus oxychloride to form the cyclic phosphoric acid ester chloride (II):
Das cyclische Phosphorsäureesterchlorid (II) wird dann in einem 2. Reaktionsschritt bei er höhter Temperatur mit einem Phenol R-OH, wobei R die eingangs beschriebene Bedeutung hat, zur Reaktion gebracht, wobei unter Abspaltung von Chlorwasserstoff der halogenfreie cyclische Phosphorsäureester (I) gebildet wird:The cyclic phosphoric acid ester chloride (II) is then in a second reaction step elevated temperature with a phenol R-OH, where R has the meaning described above has brought to reaction, with the elimination of hydrogen chloride the halogen-free cyclic phosphoric acid ester (I) is formed:
Die Umsetzungen können in geeigneten inerten Lösungsmitteln, wie Aromaten, Aliphaten, Cycloaliphaten oder Chloraliphaten, und in Gegenwart geeigneter tertiärer Amine, wie Triethylamin oder Pyridin, sowie in Gegenwart geeigneter Katalysatoren, wie Aluminium chlorid, durchgeführt werden.The reactions can be carried out in suitable inert solvents, such as aromatics, aliphatics, Cycloaliphatics or chloroaliphatics, and in the presence of suitable tertiary amines, such as Triethylamine or pyridine, and in the presence of suitable catalysts, such as aluminum chloride.
Die Umsetzungen können bei Normaldruck oder unter vermindertem Druck durchgeführt werden.The reactions can be carried out under normal pressure or under reduced pressure will.
Die Erfindung betrifft weiterhin die Verwendung der erfindungsgemäßen halogenfreien cy clischen Phosphorsäureester als Flammschutzmittel.The invention further relates to the use of the halogen-free cy according to the invention Clical phosphoric acid esters as flame retardants.
In einem ersten Reaktionsschritt wurden 208 g 2,2-Dimethyl-1,3-propandiol mit 306 g Phosphoroxichlorid [analog Verfahrensweise A aus J. Org. Chem. 24, 632 (1959)] zum 2-Chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan umgesetzt. Das erhaltene Rohpro dukt wurde aus Toluol/Cyclohexan umkristallisiert.In a first reaction step, 208 g of 2,2-dimethyl-1,3-propanediol with 306 g Phosphorus oxychloride [analogous to procedure A from J. Org. Chem. 24, 632 (1959)] for 2-Chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan implemented. The Rohpro received product was recrystallized from toluene / cyclohexane.
Für den nächsten Reaktionsschritt wurden dann 184,5 g (1 Mol) dieses Produkts in einem Rührreaktor in 1 l Toluol suspendiert, mit 108 g (1 Mol) 4-Methylphenol und 1,5 g Alumi niumchlorid (wasserfrei) versetzt und unter Rühren im Temperaturbereich von 20-110°C im Verlauf von 5 Stunden zur Reaktion gebracht.For the next reaction step, 184.5 g (1 mol) of this product were then added in one Stirred reactor suspended in 1 liter of toluene, with 108 g (1 mol) of 4-methylphenol and 1.5 g of aluminum added sodium chloride (anhydrous) and with stirring in the temperature range of 20-110 ° C. reacted over 5 hours.
Nachdem die Hälfte des Toluols im Vakuum abdestilliert worden war, wurden 500 ml
Cyclohexan zugesetzt. Dann wurde unter Rühren abgekühlt, wobei sich ein feinkristalliner
Feststoff abschied, der nach Filtration aus Toluol/Cyclohexan umkristallisiert wurde.
Es wurden 207 g eines farblosen, kristallinen Produkts mit dem Schmelzpunkt 95°C erhal
ten, dessen Elementaranalyse folgende Werte ergab:
Kohlenstoff: 56,3% (theoretisch für C₁₂H₁₇O₄P: 56,2%)
Wasserstoff: 6,5% (theoretisch für C₁₂H₁₇O₄P: 6,7%)
Phosphor: 12,1% (theoretisch für C₁₂H₁₇O₄P: 12,1%)After half of the toluene was distilled off in vacuo, 500 ml of cyclohexane was added. The mixture was then cooled with stirring, a finely crystalline solid separating out, which was recrystallized from toluene / cyclohexane after filtration. 207 g of a colorless, crystalline product with a melting point of 95 ° C. were obtained, the elemental analysis of which gave the following values:
Carbon: 56.3% (theoretically for C₁₂H₁₇O₄P: 56.2%)
Hydrogen: 6.5% (theoretically for C₁₂H₁₇O₄P: 6.7%)
Phosphorus: 12.1% (theoretically for C₁₂H₁₇O₄P: 12.1%)
Nach den obigen Analysenwerten sowie der ¹H-NMR-Analyse (Abb. 1) und der ³¹P-NMR-Analyse (Abb. 2) handelt es sich um das Produkt 5,5-Dimethyl-2-(4-methyl)phenoxy-2-oxo-1,3,2-dioxaphosphorinan.According to the above analysis values as well as the 1 H-NMR analysis ( Fig. 1) and the 31 P-NMR analysis ( Fig. 2), the product is 5,5-dimethyl-2- (4-methyl) phenoxy-2 -oxo-1,3,2-dioxaphosphorinane.
Zunächst wurde wie in Beispiel 1 beschrieben 83,2 g 2,2-Dimethyl-1,3-propandiol mit
123 g Phosphoroxichlorid zum 2-Chloro-5,5-dimethyl-2-oxo-1,3,2-dioxphosphorinan um
gesetzt. Im nächsten Reaktionsschritt wurden dann 97,6 g 3,4-Dimethylphenol, 250 ml To
luol und 1,5 g Aluminiumchlorid (wasserfrei) dazugegeben und unter Rühren während
12 h auf Rückflußtemperatur erhitzt. Der kristalline Feststoff wurde abgenutscht und mit
Wasser gereinigt.
Es wurden 161 g eines weißen Feststoffs mit einer Reinheit von 99,8% und einem
Schmelzpunkt von 121°C erhalten. Nach ³¹P-NMR und Elementaranalyse handelt es sich
um das Produkt 5,5-Dimethyl-2-(3,4-dimethyl)phenoxy-2-oxo-1,3,2-dioxaphosphorinan.First, as described in Example 1, 83.2 g of 2,2-dimethyl-1,3-propanediol was reacted with 123 g of phosphorus oxychloride to give 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxphosphorinane . In the next reaction step, 97.6 g of 3,4-dimethylphenol, 250 ml of toluene and 1.5 g of aluminum chloride (anhydrous) were then added and the mixture was heated to reflux temperature for 12 hours with stirring. The crystalline solid was suction filtered and cleaned with water.
161 g of a white solid with a purity of 99.8% and a melting point of 121 ° C. were obtained. According to 31 P-NMR and elemental analysis, the product is 5,5-dimethyl-2- (3,4-dimethyl) phenoxy-2-oxo-1,3,2-dioxaphosphorinane.
Zunächst wurde wie in Beispiel 1 beschrieben 104 g 2,2-Dimethyl-1,3-propandiol mit 154 g Phosphoroxichlorid zum 2-Chloro-5,5-dimethyl-2-oxo-1,3,2-dioxphosphorinan um gesetzt. Im nächsten Reaktionsschritt wurden dann 122 g 2,4-Dimethylphenol, 250 ml To luol und 1,8 g Aluminiumchlorid (wasserfrei) dazugegeben und unter Rühren während 7 h auf Rückflußtemperatur erhitzt. Anschließend wurden 12 g 2,4-Dimethylphenol und 1,35 g Aluminiumchlorid (wasserfrei) in 20 ml Toluol nachdosiert und nochmals 7 h auf Rückfluß erhitzt. Es wurde eine gelartige Masse erhalten, aus der das Produkt 5,5-Dimethyl-2-(2,4-dimethyl)phenoxy-2-oxo-1,3,2-dioxaphosphorinan während einer Wo che auskristallisierte.First, as described in Example 1, 104 g of 2,2-dimethyl-1,3-propanediol were added 154 g of phosphorus oxychloride to 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxphosphorinane set. In the next reaction step, 122 g of 2,4-dimethylphenol, 250 ml of To toluene and 1.8 g of aluminum chloride (anhydrous) were added and the mixture was stirred for 7 hours heated to reflux temperature. Then 12 g of 2,4-dimethylphenol and 1.35 g Aluminum chloride (anhydrous) was added in 20 ml of toluene and refluxed for a further 7 h heated. A gel-like mass was obtained from which the product 5,5-Dimethyl-2- (2,4-dimethyl) phenoxy-2-oxo-1,3,2-dioxaphosphorinane during one week che crystallized.
Zunächst wurde wie in Beispiel 1 beschrieben 112,3 g 2,2-Dimethyl-1,3-propandiol mit 166 g Phosphoroxichlorid zum 2-Chloro-5,5-dimethyl-2-oxo-1,3,2-dioxphosphorinan um gesetzt. Im nächsten Reaktionsschritt wurden dann 131,7 g 2,3-Dimethylphenol, 500 ml Toluol und 2,5 g Aluminiumchlorid (wasserfrei) dazugegeben und unter Rühren während 12 h auf Rückflußtemperatur erhitzt. Durch Zugabe von 1 l Cyclohexan wurde das Produkt ausgefällt und abgenutscht.First, as described in Example 1, 112.3 g of 2,2-dimethyl-1,3-propanediol were added 166 g of phosphorus oxychloride to 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxphosphorinane set. In the next reaction step, 131.7 g of 2,3-dimethylphenol, 500 ml Toluene and 2.5 g of aluminum chloride (anhydrous) are added and stirring is continued Heated to reflux temperature for 12 h. The product was obtained by adding 1 l of cyclohexane precipitated and sucked off.
Es wurden 193 g eines weißen Feststoffs mit einem Schmelzpunkt von 79°C erhalten. Nach ³¹P-NMR und Elementaranalyse handelt es sich um das Produkt 5,5-Dimethyl-2-(2,3-dimethyl)phenoxy-2-oxo-1,3,2-dioxaphosphorinan.193 g of a white solid with a melting point of 79 ° C. were obtained. According to 31 P-NMR and elemental analysis, it is the product 5,5-dimethyl-2- (2,3-dimethyl) phenoxy-2-oxo-1,3,2-dioxaphosphorinane.
Claims (6)
R = 2-Methylphenyl, 3-Methylphenyl, 4-Methylphenyl, 2,3-Dimethylphenyl, 2,4-Dimethylphenyl, 2,5-Dimethylphenyl oder 3,4-Dimethylphenyl.1. Halogen-free cyclic phosphoric acid esters of the general formula (I) With
R = 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl or 3,4-dimethylphenyl.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996121880 DE19621880A1 (en) | 1996-05-31 | 1996-05-31 | Halogen-free cyclic phosphate ester(s) useful as flame retardants |
| EP96118176A EP0779294A1 (en) | 1995-12-15 | 1996-11-13 | Halogen-free cyclic phosphoric acid esters and process for their preparation |
| JP33357896A JPH09183786A (en) | 1995-12-15 | 1996-12-13 | Halogen-free cyclic phosphoric acid ester and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996121880 DE19621880A1 (en) | 1996-05-31 | 1996-05-31 | Halogen-free cyclic phosphate ester(s) useful as flame retardants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19621880A1 true DE19621880A1 (en) | 1997-12-04 |
Family
ID=7795786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1996121880 Withdrawn DE19621880A1 (en) | 1995-12-15 | 1996-05-31 | Halogen-free cyclic phosphate ester(s) useful as flame retardants |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19621880A1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0449689A1 (en) * | 1990-03-26 | 1991-10-02 | Elf Atochem S.A. | Fireproofed polymeric compositions, process for their preparation and their use for the manufacture of fireproofed industrial items |
| EP0617042A1 (en) * | 1993-03-16 | 1994-09-28 | Daihachi Chemical Industry Co., Ltd. | Organic phosphorus compounds and flame-retarded resin compositions containing the same |
-
1996
- 1996-05-31 DE DE1996121880 patent/DE19621880A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0449689A1 (en) * | 1990-03-26 | 1991-10-02 | Elf Atochem S.A. | Fireproofed polymeric compositions, process for their preparation and their use for the manufacture of fireproofed industrial items |
| EP0617042A1 (en) * | 1993-03-16 | 1994-09-28 | Daihachi Chemical Industry Co., Ltd. | Organic phosphorus compounds and flame-retarded resin compositions containing the same |
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