CA2058762A1 - 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
- CA2058762A1 CA2058762A1 CA002058762A CA2058762A CA2058762A1 CA 2058762 A1 CA2058762 A1 CA 2058762A1 CA 002058762 A CA002058762 A CA 002058762A CA 2058762 A CA2058762 A CA 2058762A CA 2058762 A1 CA2058762 A1 CA 2058762A1
- Authority
- CA
- Canada
- Prior art keywords
- aryl
- carbon atoms
- formula
- phosphonites
- radical
- 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
- 238000000465 moulding Methods 0.000 title abstract 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 title abstract 2
- 229920000098 polyolefin Polymers 0.000 title abstract 2
- 150000007860 aryl ester derivatives Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000463 material Substances 0.000 title 1
- 229920003023 plastic Polymers 0.000 title 1
- 239000004033 plastic Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 4
- -1 aryl phosphonites Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 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
- 125000005002 aryl methyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 238000010137 moulding (plastic) Methods 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 238000002360 preparation method Methods 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)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
A process for the preparation of aryl phosphonites of the formula V
(see formula I) in which A is non-existent or a direct bond or a divalent hydrocarbon bridge having 1 to 6 carbon atoms which may be substituted by groups mentioned further below under R1, or is a hetero atom, cycloalkylidene having 4 to 8 carbon atoms or phenylalkylidene having 7 to 12 carbon atoms, n is 1 or 2, R1 as monovalent radical is certain non-aromatic or aromatic hydrocarbon radicals, in which the aromatic radicals are substituents such as alkyl, alkoxy, alkylthio, dialkylamino, aryl, aryloxy or halogen, and as divalent radical a phenylene or naphthylene radical, which may carry non-aromatic hydrocarbon radicals as substituents, R2 is a non-aromatic hydrocarbon radical having 1 to 18 carbon atoms, aryl, arylmethyl, arylethyl or arylisopropyl, in which the aryl in each case contains 6 to carbon atoms, and R3 is hydrogen or a group mentioned under R2, in which process in a first step a hydrocarbon halide R1(-Hal)n, in which R1 has the abovementioned meaning, n is = 1 or 2 and the halogen has an atomic weight of at least 35, is reacted under Grignard conditions with at least molar amounts of magnesium to give the corresponding Grignard compounds R1(MgHal)n and these compounds are reacted in a second step with bisaryl halophosphonites of the formula VI
(see formula I) , in which R2, R3 and Hal ha,e the abovementioned meaning, with the formation of the aryl phosphonites V.
The invention further relates to a plastic molding composition, in particular a polyolefin molding composition containing aryl phosphonites of the formula V.
The molding composition is distinguished by improved properties compared with those molding compositions containing phosphonites prepared by the prior art.
(see formula I) in which A is non-existent or a direct bond or a divalent hydrocarbon bridge having 1 to 6 carbon atoms which may be substituted by groups mentioned further below under R1, or is a hetero atom, cycloalkylidene having 4 to 8 carbon atoms or phenylalkylidene having 7 to 12 carbon atoms, n is 1 or 2, R1 as monovalent radical is certain non-aromatic or aromatic hydrocarbon radicals, in which the aromatic radicals are substituents such as alkyl, alkoxy, alkylthio, dialkylamino, aryl, aryloxy or halogen, and as divalent radical a phenylene or naphthylene radical, which may carry non-aromatic hydrocarbon radicals as substituents, R2 is a non-aromatic hydrocarbon radical having 1 to 18 carbon atoms, aryl, arylmethyl, arylethyl or arylisopropyl, in which the aryl in each case contains 6 to carbon atoms, and R3 is hydrogen or a group mentioned under R2, in which process in a first step a hydrocarbon halide R1(-Hal)n, in which R1 has the abovementioned meaning, n is = 1 or 2 and the halogen has an atomic weight of at least 35, is reacted under Grignard conditions with at least molar amounts of magnesium to give the corresponding Grignard compounds R1(MgHal)n and these compounds are reacted in a second step with bisaryl halophosphonites of the formula VI
(see formula I) , in which R2, R3 and Hal ha,e the abovementioned meaning, with the formation of the aryl phosphonites V.
The invention further relates to a plastic molding composition, in particular a polyolefin molding composition containing aryl phosphonites of the formula V.
The molding composition is distinguished by improved properties compared with those molding compositions containing phosphonites prepared by the prior art.
Applications Claiming Priority (7)
| 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. |
| DEP3916502.7 | 1989-05-20 | ||
| DEP3923492.4 | 1989-07-15 | ||
| DE3923492A DE3923492A1 (en) | 1989-05-20 | 1989-07-15 | New phosphonous acid aryl ester(s) |
| DEP4014428.3 | 1990-05-05 | ||
| DE4014428A DE4014428A1 (en) | 1989-05-20 | 1990-05-05 | New phosphonous acid aryl ester(s) |
| PCT/EP1990/000787 WO1990014349A2 (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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2058762A1 true CA2058762A1 (en) | 1990-11-21 |
| CA2058762C CA2058762C (en) | 2001-05-08 |
Family
ID=27199597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002058762A Expired - Fee Related CA2058762C (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 (3)
| 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. |
| 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 |
-
1990
- 1990-05-16 AT AT90907020T patent/ATE111915T1/en not_active IP Right Cessation
- 1990-05-16 JP JP2507347A patent/JP3004713B2/en not_active Expired - Fee Related
- 1990-05-16 WO PCT/EP1990/000787 patent/WO1990014349A2/en active IP Right Grant
- 1990-05-16 CA CA002058762A patent/CA2058762C/en not_active Expired - Fee Related
- 1990-05-16 AU AU56539/90A patent/AU635537B2/en not_active Ceased
- 1990-05-16 DE DE59007280T patent/DE59007280D1/en not_active Expired - Fee Related
- 1990-05-16 KR KR1019910701632A patent/KR0169086B1/en not_active Expired - Fee Related
- 1990-05-16 ES ES90907020T patent/ES2064730T3/en not_active Expired - Lifetime
- 1990-05-16 EP EP90907020A patent/EP0472564B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2058762C (en) | 2001-05-08 |
| WO1990014349A2 (en) | 1990-11-29 |
| WO1990014349A3 (en) | 1991-02-21 |
| AU5653990A (en) | 1990-12-18 |
| JPH04507092A (en) | 1992-12-10 |
| DE59007280D1 (en) | 1994-10-27 |
| AU635537B2 (en) | 1993-03-25 |
| KR0169086B1 (en) | 1999-03-20 |
| JP3004713B2 (en) | 2000-01-31 |
| EP0472564A1 (en) | 1992-03-04 |
| ES2064730T3 (en) | 1995-02-01 |
| EP0472564B1 (en) | 1994-09-21 |
| ATE111915T1 (en) | 1994-10-15 |
| KR920701218A (en) | 1992-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4093641A (en) | Preparation of silylalkyl esters of phosphorus | |
| US4005117A (en) | Organosilane compounds | |
| US4005118A (en) | Organosilane compounds | |
| AU637268B2 (en) | Self-extinguishing polymeric compositions | |
| US4005119A (en) | Organosilane compounds | |
| US4297492A (en) | Phenolic-1,3,5-triazines | |
| CA2058762A1 (en) | Arylesters of phosphonous acid, process for preparing them and their use to stabilize plastics, in particular polyolefin moulding materials | |
| TW297822B (en) | ||
| USRE32504E (en) | Room temperature stable organopolysiloxane compositions | |
| CA2086616A1 (en) | 6-Aryl-6H-Dibenzo[c,e][1,2] Oxaphosphorines, a Process for Their Preparation, and Their Use for Stabilizing Plastics, in Particular Polyolefin Molding Compositions | |
| US2754312A (en) | Aminoalkyl cyclopolysiloxane compositions and their preparation | |
| EP0139221A3 (en) | Substituted dihydroazepines useful as calcium channel blockers, methods for preparing and compositions containing the same | |
| KR940011569A (en) | Cycloolefin Polymer Molding Composition with Improved Stability against Chemical Degradation | |
| US4417071A (en) | Phenols useful as stabilizers | |
| US4402882A (en) | Process for the production of diphosphaspiro compounds | |
| KR880007635A (en) | New complexes of bismuth or antimony halides and amines suitable as flame retardants for polymers and polymer compositions containing them | |
| EP0551153B1 (en) | Derivatives of 2,4-diamino-1,3,5-triazinyl-6-phosphonic acid | |
| US3454677A (en) | Inner salts of aminophosphonates and preparation thereof | |
| EP0335262B1 (en) | Phosphite compounds | |
| EP0551154B1 (en) | Self-extinguishing polymeric compositions | |
| US3222369A (en) | Phenylsiloxanediol amine complexes and process for their production | |
| US3346588A (en) | Silicon-substituted pyrroles | |
| US2864845A (en) | Carbon functional organo-silicon phosphonates | |
| DE68926016D1 (en) | Halogeno-4-methylpyrazoles and process for their preparation | |
| DE3568579D1 (en) | Preparation of intermediates containing phosphorus for herbicidal uses |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |