AU5653990A - Arylesters of phosphonous acid, process for preparing them and their use to stabilize plastics, in particular polyolefin moulding materials - Google Patents
Arylesters of phosphonous acid, process for preparing them and their use to stabilize plastics, in particular polyolefin moulding materialsInfo
- Publication number
- AU5653990A AU5653990A AU56539/90A AU5653990A AU5653990A AU 5653990 A AU5653990 A AU 5653990A AU 56539/90 A AU56539/90 A AU 56539/90A AU 5653990 A AU5653990 A AU 5653990A AU 5653990 A AU5653990 A AU 5653990A
- Authority
- AU
- Australia
- Prior art keywords
- carbon atoms
- phosphonous acid
- aryl
- residue
- aromatic
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title abstract 5
- 238000000465 moulding Methods 0.000 title abstract 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 title abstract 3
- 150000007860 aryl ester derivatives Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 229920003023 plastic Polymers 0.000 title abstract 2
- 239000004033 plastic Substances 0.000 title abstract 2
- 229920000098 polyolefin Polymers 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- -1 phosphonous acid arylester Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 238000010420 art technique Methods 0.000 abstract 1
- 125000005002 aryl methyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 150000002901 organomagnesium compounds Chemical class 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
-
- 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
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4841—Aromatic acids or derivatives (P-C aromatic linkage)
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/485—Polyphosphonous acids or derivatives
-
- 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
- C07F9/657163—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
- C07F9/65719—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)phosphonous acid derivative
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Process for preparing aryl esters of phosphonous acid of formula (V), where A is non-existent or a direct bond or a divalent hydrocarbon bridge with 1 to 6 carbon atoms, which can be substituted by the groups mentioned below, or a heteroatom, cycloalkylidene with 4 to 8 carbon atoms or phenylalkylidene with 7 to 12 carbon atoms, n is equal to 1 or 2, R<1> as a monovalent residue denotes certain non-aromatic or aromatic hydrocarbon residues, the aromatic residues denoting substituents such as alkyl, alkoxy, alkylthio, dialkylamino, aryl, aryloxy or halogen, and as a divalent residue denotes a phenylene or naththylene residue, which can carry non-aromatic hydrocarbon residues as substituents, R<2> is a non-aromatic hydrocarbon residue with 1 to 18 carbon atoms, aryl, arylmethyl, arylethyl or arylisopropyl, each aryl containing 6 to 10 carbon atoms, and R<3> denotes hydrogen or one of the groups mentioned under R<2>. In a first stage a halogenated hydrocarbon R<1>(-Hal)n, in which R<1> has the above-mentioned meaning, n = 1 or 2, and the halogen has an atomic weight of at least 35, is converted under Grignard conditions with at least molar quantities of magnesium to the corresponding organomagnesium compounds R<1>(MgHal)n. These are reacted in a second stage with phosphoric acid-bis-arylester halides of formula (VI), where R<2>, R<3> and Hal have the above-mentioned meanings, to form the phosphonous acid arylester (V). The invention also relates to a plastics moulding material, in particular a polyolefin moulding material, containing the phosphonous acid arylester of formula (V). The properties of the moulding material are superior to those of materials which contain phosphonites produced by prior art techniques.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3916502A DE3916502A1 (en) | 1989-05-20 | 1989-05-20 | New and known di:aryl - with tetra:alkyl di:phosphinite cpds., are prepd. as stabilisers for plastics by reacting di:aryl halo-phosphonite with grignard cpd. |
| DE3916502 | 1989-05-20 | ||
| DE3923492A DE3923492A1 (en) | 1989-05-20 | 1989-07-15 | New phosphonous acid aryl ester(s) |
| DE3923492 | 1989-07-15 | ||
| DE4014428A DE4014428A1 (en) | 1989-05-20 | 1990-05-05 | New phosphonous acid aryl ester(s) |
| DE4014428 | 1990-05-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5653990A true AU5653990A (en) | 1990-12-18 |
| AU635537B2 AU635537B2 (en) | 1993-03-25 |
Family
ID=27199597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU56539/90A Ceased AU635537B2 (en) | 1989-05-20 | 1990-05-16 | Arylesters of phosphonous acid, process for preparing them and their use to stabilize plastics, in particular polyolefin moulding materials |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0472564B1 (en) |
| JP (1) | JP3004713B2 (en) |
| KR (1) | KR0169086B1 (en) |
| AT (1) | ATE111915T1 (en) |
| AU (1) | AU635537B2 (en) |
| CA (1) | CA2058762C (en) |
| DE (1) | DE59007280D1 (en) |
| ES (1) | ES2064730T3 (en) |
| WO (1) | WO1990014349A2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2250990A (en) * | 1990-12-21 | 1992-06-24 | Ciba Geigy Ag | Substituted dibenzo[d,g][1,3,2]dioxaphosphocins |
| TW208017B (en) * | 1991-07-26 | 1993-06-21 | Hoechst Ag | |
| US11767413B2 (en) | 2019-02-21 | 2023-09-26 | Clariant International Ltd | Phosphonite compounds as process stabilizers |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH633296A5 (en) * | 1977-08-19 | 1982-11-30 | Sandoz Ag | METHOD FOR PRODUCING 4- (N, N-DIALKYLAMINO-) PHENYLPHOSPHONITES. |
| SU897797A1 (en) * | 1980-04-07 | 1982-01-15 | Всесоюзный Научно-Исследовательский И Проектный Институт Полимерных Продуктов | Composition based on polytrichlorobutadiene |
| DE3373658D1 (en) * | 1983-06-08 | 1987-10-22 | Adeka Argus Chemical Co Ltd | Hindered bisphenol diphosphonites and stabilized synthetic resin compositions containing the same |
| FR2562543B1 (en) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | NOVEL CYCLIC PHOSPHONITES, THEIR PREPARATION AND APPLICATIONS |
| JP3479544B2 (en) * | 1993-10-22 | 2003-12-15 | スター精密株式会社 | Printing device |
-
1990
- 1990-05-16 AU AU56539/90A patent/AU635537B2/en not_active Ceased
- 1990-05-16 KR KR1019910701632A patent/KR0169086B1/en not_active IP Right Cessation
- 1990-05-16 WO PCT/EP1990/000787 patent/WO1990014349A2/en active IP Right Grant
- 1990-05-16 DE DE59007280T patent/DE59007280D1/en not_active Expired - Fee Related
- 1990-05-16 EP EP90907020A patent/EP0472564B1/en not_active Expired - Lifetime
- 1990-05-16 AT AT90907020T patent/ATE111915T1/en not_active IP Right Cessation
- 1990-05-16 ES ES90907020T patent/ES2064730T3/en not_active Expired - Lifetime
- 1990-05-16 JP JP2507347A patent/JP3004713B2/en not_active Expired - Fee Related
- 1990-05-16 CA CA002058762A patent/CA2058762C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04507092A (en) | 1992-12-10 |
| KR0169086B1 (en) | 1999-03-20 |
| CA2058762C (en) | 2001-05-08 |
| WO1990014349A3 (en) | 1991-02-21 |
| CA2058762A1 (en) | 1990-11-21 |
| AU635537B2 (en) | 1993-03-25 |
| WO1990014349A2 (en) | 1990-11-29 |
| KR920701218A (en) | 1992-08-11 |
| DE59007280D1 (en) | 1994-10-27 |
| EP0472564B1 (en) | 1994-09-21 |
| ES2064730T3 (en) | 1995-02-01 |
| EP0472564A1 (en) | 1992-03-04 |
| ATE111915T1 (en) | 1994-10-15 |
| JP3004713B2 (en) | 2000-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Assignment registered |
Free format text: CLARIANT GMBH |