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CH603674A5 - Derivs of bis (2-(oxo or thiono)-1,3,2-dioxaphosphorinanyl)oxide - Google Patents

Derivs of bis (2-(oxo or thiono)-1,3,2-dioxaphosphorinanyl)oxide

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Publication number
CH603674A5
CH603674A5 CH131877A CH131877A CH603674A5 CH 603674 A5 CH603674 A5 CH 603674A5 CH 131877 A CH131877 A CH 131877A CH 131877 A CH131877 A CH 131877A CH 603674 A5 CH603674 A5 CH 603674A5
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Switzerland
Prior art keywords
sep
hydrogen
alkyl radical
carbon atom
formula
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Application number
CH131877A
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German (de)
Inventor
Claudine Mauric
Rainer Wolf
Original Assignee
Sandoz Ag
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Publication date
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH131877A priority Critical patent/CH603674A5/en
Publication of CH603674A5 publication Critical patent/CH603674A5/en

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    • 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
    • C08K5/5398—Phosphorus bound to sulfur
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/098—Esters of polyphosphoric acids or anhydrides
    • 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
    • C07F9/657109—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 esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
    • C07F9/657136—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 esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) the molecule containing more than one cyclic phosphorus atom
    • 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
    • C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
    • 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

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  • 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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Derivs of bis (2-(oxo or thiono)-1,3,2-dioxaphosphorinanyl)oxide flame proofing agents particularly for regenerated cellulose

Description

  

  
 



  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Phosphorverbindungen der Formel
EMI1.1     
 worin X unabhängig voneinander Sauerstoff oder Schwefel,   Rl    Wasserstoff, einen Alkylrest mit 1-4 C-Atomen, oder Phenyl, R2 Wasserstoff, einen Alkylrest mit 1-4 C-Atomen, oder   Rl    und R2 zusammen mit dem gemeinsamen C-Atom einen Cyclohexyliden-, Cyclohexenyliden- oder 3,4-Dibromcyclohexylidenring, R3 und Rs unabhängig voneinander Wasserstoff oder einen Alkylrest mit 1-4 C-Atomen, R4 Wasserstoff oder Methyl, wobei a) mindestens einer der Substituenten   Rl,    R2, R3, R4 und Rs von Wasserstoff verschieden ist, b) wenn   Rl    und R2 einen Ring zusammen mit dem gemeinsamen C-Atom bilden, R3, R4 und Rs immer Wasserstoff, c) wenn X = Sauerstoff,

   R1 und R2 immer zusammen mit dem gemeinsamen C-Atom einen der genannten Ringe, und d) wenn   Rl    und'oder R2 einen Alkylrest bedeuten, mindestens einer der Substituenten R3, R4, Rs von Wasserstoff verschieden ist, bedeuten, welches dadurch gekennzeichnet ist, dass man 2 Mol einer Verbindung der Formel
EMI1.2     
   worin R1, R2, R3, R4, R5 und X die obige Bedeutung haben,    mit 1 Mol Wasser in Gegenwart einer Base wie Pyridin, hydrolysiert.



   Bevorzugt ist das Verfahren zur Herstellung von Verbindungen der Formel
EMI1.3     
 worin X' Sauerstoff oder Schwefel,   R'l    und R'2 zusammen mit dem gemeinsamen C-Atom einen Cyclohexyliden-, Cyclohexenyliden- oder   3 ,4-Dibromcyclohe-    xylidenring bedeuten.



   Bevorzugt ist das Verfahren zur Herstellung von Verbindungen der Formel
EMI1.4     
 worin X' Sauerstoff oder Schwefel,   R"l    und R"2 zusammen mit dem gemeinsamen C-Atom einen Cyclohexyliden- oder   3 ,4-Dibromcyclohexylidenring    bedeuten.



   Die Reaktionsbedingungen sind aus analogen Reaktionen bekannt. Die Verbindungen der Formel (II) stellt man in an sich bekannter Weise her.



     Rl    bedeutet vorzugsweise   R'l    bzw.   R"l,    R2 bedeutet vorzugsweise R'2, vorzugsweise R"2, X bedeutet vorzugsweise   X'.   



   Bilden   Rl    und R2 zusammen mit dem gemeinsamen C Atom einen Ring, so bedeutet dieser vorzugsweise Cyclohexyliden, Cyclohexenyliden- oder 3 ,4-Dibromcyclohexyliden, vorzugsweise Cyclohexenyliden oder 3,4-Dibromcyclohexyliden.



   Die erfindungsgemässen Verbindungen sind geeignet für das flammhemmende Ausrüsten von polymeren organischen Materialien, vorzugsweise regenerierter Cellulose.



   In den folgenden Beispielen bedeuten die Teile Gewichtsteile, die Prozente Gewichtsprozente.



   Beispiel I
In einem Reaktionskolben werden 279,5 Teile Thiophosphorylchlorid in 2500 Teilen Benzol gelöst und bei 200 mit 261 Teilen Pyridin versetzt. Innerhalb von 15 Minuten werden dann 498,2 Teile   1, 1-Dihydroxymethyl-3 ,4-dibromcyclohexan    bei   20-25o    zugegeben und die Mischung 5 Stunden bei   40O    unter Stickstoff gerührt. Anschliessend wird auf 200 abgekühlt, filtriert und das Filtrat im Vakuum eingedampft. Man erhält 634.3 Teile einer hochviskosen Masse. 622 Teile dieser Masse  werden in 800 Teilen Pyridin gelöst und bei 200 mit 14 Teilen Wasser versetzt. Man lässt das Gemisch 21 Stunden bei 30 bis 380 reagieren, kühlt dann auf 200 ab, filtriert den entstandenen Niederschlag ab und wäscht ihn gut mit Wasser aus.

  Nach Trocknung erhält man 440 Teile einer Verbindung der Formel 3 der Tabelle I, welche bei 2280 unter Zersetzung schmilzt.



   In analoger Weise stellt man die Verbindungen der folgenden Tabelle 1 her.



  Tabelle 1
EMI2.1     


<tb> Bsp. <SEP> Struktur <SEP> Schmelzpunkt
<tb> No.
<tb>



   <SEP> 1CH <SEP> /C1 <SEP> 2O\ <SEP> 24M20
<tb>  <SEP> ( <SEP> \C <SEP> 5 <SEP> 2
<tb>  <SEP> Oo <SEP> cHos"
<tb>  <SEP> 2 <SEP> 2
<tb>  <SEP> 2 <SEP> -CH3, <SEP> -CH <SEP> CH <SEP> 2O <SEP> 187-188"
<tb>  <SEP> CH/C; <SEP> /5/
<tb>  <SEP> \ <SEP> CH <SEP> -CH <SEP> 2 <SEP> 2
<tb>  <SEP> Br
<tb>  <SEP> 4 <SEP> /CH <SEP> -CH2s <SEP> oCH20s <SEP> ss
<tb>  <SEP> 3 <SEP> CHCH <SEP> -cH2¸ <SEP> 2280 <SEP> unter
<tb>  <SEP> Br <SEP> 2 <SEP> 2 <SEP> C <SEP> 2 <SEP> S <SEP>  <  <SEP> Zersetzung
<tb>  <SEP> Br' <SEP> 2 <SEP> cH2o11
<tb>  <SEP> 2
<tb>  <SEP> 4 <SEP> CH3 <SEP> c%CH <SEP> 2Op <SEP> 101080
<tb>  <SEP> cHM <SEP> CHO" <SEP> ss
<tb>  <SEP> 3 <SEP> s
<tb>  <SEP> n-C3H7 <SEP> 2
<tb>  <SEP> cH3M <SEP> CH <SEP> 20Np
<tb>  <SEP> CH./C
<tb>  <SEP> 3 <SEP> 1
<tb>  <SEP> 3 <SEP> 7 <SEP> 2
<tb>  <SEP> p <SEP> 0
<tb>  <SEP> 6 <SEP> (C21i5\ <SEP> /Cl] <SEP> 2 \ <SEP> I1 <SEP> (flüssig)
<tb>  <SEP>  

   s
<tb>  <SEP> n-C <SEP> 3H7 <SEP> 2
<tb>  <SEP> CH
<tb>  <SEP> 3
<tb>  <SEP> 7 <SEP> CII <SEP> 0¸ <SEP> lS9-160
<tb>  <SEP> H2C <SEP> c-o <SEP> 0
<tb>  <SEP> CII <SEP> CII
<tb>  <SEP> 2
<tb>    Tabelle 1 (Fortsetzung)
EMI3.1     


<tb>  <SEP> Bsp. <SEP> Struktur <SEP> Schmelzpunkt
<tb>  <SEP> No.
<tb>



   <SEP> 8 <SEP> CCII <SEP> 20% <SEP> 161-163Q
<tb>  <SEP>  <  <SEP> 2 <SEP> \ <SEP> CH <SEP> O <SEP> S <SEP> 2
<tb>  <SEP> C <SEP> H3 <SEP> 2
<tb>  <SEP> 9 <SEP> IIC <SEP> CII <SEP> ' <SEP> N <SEP> CH <SEP> 20Np <SEP> 239-M10
<tb>  <SEP> 9 <SEP> 9 <SEP> \ <SEP> CH <SEP> · <SEP> CEI2 <SEP> 0ll
<tb>  <SEP> 2 <SEP> 2 <SEP> 202
<tb>  <SEP> g <SEP> / <SEP> C <SEP> H <SEP> CH <SEP> 2 <SEP> \ <SEP> eCII2 <SEP> 0 <SEP> \ <SEP> ss
<tb> 10 <SEP> Br-CII <SEP> c <SEP> p <SEP> 1400 <SEP> unter
<tb>  <SEP> H,-CH2 <SEP> CH2 <SEP> Ov <SEP> Zusetzung
<tb>  



  
 



  The present invention relates to a process for the preparation of phosphorus compounds of the formula
EMI1.1
 wherein X is independently oxygen or sulfur, Rl is hydrogen, an alkyl radical with 1-4 C atoms, or phenyl, R2 is hydrogen, an alkyl radical with 1-4 C atoms, or Rl and R2 together with the common C atom is a cyclohexylidene -, Cyclohexenylidene or 3,4-dibromocyclohexylidene ring, R3 and Rs independently of one another are hydrogen or an alkyl radical with 1-4 C atoms, R4 is hydrogen or methyl, where a) at least one of the substituents R1, R2, R3, R4 and Rs of Hydrogen is different, b) if Rl and R2 form a ring together with the common carbon atom, R3, R4 and Rs always hydrogen, c) if X = oxygen,

   R1 and R2 always together with the common carbon atom one of the rings mentioned, and d) when Rl and 'or R2 are an alkyl radical, at least one of the substituents R3, R4, Rs is different from hydrogen, which is characterized by that you have 2 moles of a compound of the formula
EMI1.2
   wherein R1, R2, R3, R4, R5 and X are as defined above, hydrolyzed with 1 mole of water in the presence of a base such as pyridine.



   The process for the preparation of compounds of the formula is preferred
EMI1.3
 where X 'is oxygen or sulfur, R'1 and R'2 together with the common carbon atom denote a cyclohexylidene, cyclohexenylidene or 3, 4-dibromocyclohexylidene ring.



   The process for the preparation of compounds of the formula is preferred
EMI1.4
 where X 'is oxygen or sulfur, R "1 and R" 2 together with the common carbon atom denote a cyclohexylidene or 3,4-dibromocyclohexylidene ring.



   The reaction conditions are known from analogous reactions. The compounds of the formula (II) are prepared in a manner known per se.



     Rl preferably means R'l or R "1, R2 preferably means R'2, preferably R" 2, X preferably means X '.



   If R1 and R2 form a ring together with the common carbon atom, this preferably denotes cyclohexylidene, cyclohexenylidene- or 3,4-dibromocyclohexylidene, preferably cyclohexenylidene or 3,4-dibromocyclohexylidene.



   The compounds according to the invention are suitable for making polymeric organic materials, preferably regenerated cellulose, flame-retardant.



   In the following examples, the parts are parts by weight and the percentages are percentages by weight.



   Example I.
279.5 parts of thiophosphoryl chloride are dissolved in 2500 parts of benzene in a reaction flask, and 261 parts of pyridine are added at 200 parts. 498.2 parts of 1,1-dihydroxymethyl-3,4-dibromocyclohexane are then added at 20-25 ° over the course of 15 minutes, and the mixture is stirred for 5 hours at 40 ° under nitrogen. It is then cooled to 200, filtered and the filtrate evaporated in vacuo. 634.3 parts of a highly viscous mass are obtained. 622 parts of this mass are dissolved in 800 parts of pyridine, and 14 parts of water are added at 200 parts. The mixture is left to react for 21 hours at 30 to 380, then cooled to 200, the precipitate formed is filtered off and washed thoroughly with water.

  After drying, 440 parts of a compound of the formula 3 in Table I are obtained, which melts at 2280 with decomposition.



   The compounds in Table 1 below are prepared in an analogous manner.



  Table 1
EMI2.1


<tb> Ex. <SEP> structure <SEP> melting point
<tb> No.
<tb>



   <SEP> 1CH <SEP> / C1 <SEP> 2O \ <SEP> 24M20
<tb> <SEP> (<SEP> \ C <SEP> 5 <SEP> 2
<tb> <SEP> Oo <SEP> cHos "
<tb> <SEP> 2 <SEP> 2
<tb> <SEP> 2 <SEP> -CH3, <SEP> -CH <SEP> CH <SEP> 2O <SEP> 187-188 "
<tb> <SEP> CH / C; <SEP> / 5 /
<tb> <SEP> \ <SEP> CH <SEP> -CH <SEP> 2 <SEP> 2
<tb> <SEP> Br
<tb> <SEP> 4 <SEP> / CH <SEP> -CH2s <SEP> oCH20s <SEP> ss
<tb> <SEP> 3 <SEP> CHCH <SEP> -cH2¸ <SEP> 2280 <SEP> under
<tb> <SEP> Br <SEP> 2 <SEP> 2 <SEP> C <SEP> 2 <SEP> S <SEP> <<SEP> Decomposition
<tb> <SEP> Br '<SEP> 2 <SEP> cH2o11
<tb> <SEP> 2
<tb> <SEP> 4 <SEP> CH3 <SEP> c% CH <SEP> 2Op <SEP> 101080
<tb> <SEP> cHM <SEP> CHO "<SEP> ss
<tb> <SEP> 3 <SEP> s
<tb> <SEP> n-C3H7 <SEP> 2
<tb> <SEP> cH3M <SEP> CH <SEP> 20Np
<tb> <SEP> CH./C
<tb> <SEP> 3 <SEP> 1
<tb> <SEP> 3 <SEP> 7 <SEP> 2
<tb> <SEP> p <SEP> 0
<tb> <SEP> 6 <SEP> (C21i5 \ <SEP> / Cl] <SEP> 2 \ <SEP> I1 <SEP> (liquid)
<tb> <SEP>

   s
<tb> <SEP> n-C <SEP> 3H7 <SEP> 2
<tb> <SEP> CH
<tb> <SEP> 3
<tb> <SEP> 7 <SEP> CII <SEP> 0¸ <SEP> lS9-160
<tb> <SEP> H2C <SEP> c-o <SEP> 0
<tb> <SEP> CII <SEP> CII
<tb> <SEP> 2
<tb> Table 1 (continued)
EMI3.1


<tb> <SEP> e.g. <SEP> structure <SEP> melting point
<tb> <SEP> No.
<tb>



   <SEP> 8 <SEP> CCII <SEP> 20% <SEP> 161-163Q
<tb> <SEP> <<SEP> 2 <SEP> \ <SEP> CH <SEP> O <SEP> S <SEP> 2
<tb> <SEP> C <SEP> H3 <SEP> 2
<tb> <SEP> 9 <SEP> IIC <SEP> CII <SEP> '<SEP> N <SEP> CH <SEP> 20Np <SEP> 239-M10
<tb> <SEP> 9 <SEP> 9 <SEP> \ <SEP> CH <SEP> · <SEP> CEI2 <SEP> 0ll
<tb> <SEP> 2 <SEP> 2 <SEP> 202
<tb> <SEP> g <SEP> / <SEP> C <SEP> H <SEP> CH <SEP> 2 <SEP> \ <SEP> eCII2 <SEP> 0 <SEP> \ <SEP> ss
<tb> 10 <SEP> Br-CII <SEP> c <SEP> p <SEP> 1400 <SEP> under
<tb> <SEP> H, -CH2 <SEP> CH2 <SEP> Ov <SEP> addition
<tb>

Claims (1)

PATENTANSPRÜCHE I. Verfahren zur Herstellung von Phosphorverbindungen der Formel EMI3.2 worin X unabhängig voneinander Sauerstoff oder Schwefel, Ri Wasserstoff, einen Alkylrest mit 1-4 C-Atomen, oder Phenyl, R2 Wasserstoff, einen Alkylrest mit 14 C-Atomen, oder Ri und R2 zusammen mit dem gemeinsamen C-Atom einen Cyclohexyliden-, Cyclohexenyliden- oder 3 ,4-Dibromcyclohe- xylidenring, R3 und Rs unabhängig voneinander Wasserstoff oder einen Alkylrest mit 14 C-Atomen, R4 Wasserstoff oder Methyl, wobei a) mindestens einer der Substituenten Rt, R2, R3, R4 und Rs von Wasserstoff verschieden ist, b) wenn Rl und R2 einen Ring zusammen mit dem gemeinsamen C-Atom bilden, Rs, R4 und Rs immer Wasserstoff, PATENT CLAIMS I. Process for the preparation of phosphorus compounds of the formula EMI3.2 wherein X independently of one another is oxygen or sulfur, Ri is hydrogen, an alkyl radical with 1-4 C atoms, or Phenyl, R2 is hydrogen, an alkyl radical with 14 carbon atoms, or Ri and R2 together with the common carbon atom form one Cyclohexylidene, cyclohexenylidene or 3, 4-dibromocyclohexylidene ring, R3 and Rs independently of one another are hydrogen or an alkyl radical with 14 carbon atoms, R4 is hydrogen or methyl, where a) at least one of the substituents Rt, R2, R3, R4 and Rs is different from hydrogen, b) when R1 and R2 form a ring form with the common carbon atom, Rs, R4 and Rs always hydrogen, c) wenn X = Sauerstoff, Rl und R2 immer zusammen mit dem gemeinsamen C-Atom einer der genannten Ringe, und d) wenn Rl und/oder Rt einen Alkylrest bedeuten, mindestens einer der Substituenten R3, R4, Rt von Wasserstoff verschieden ist, bedeuten, dadurch gekennzeichnet, dass man 2 Mol einer Verbindung der Formel EMI3.3 worin Rt, Rt, R3, R4, Rt und X die obige Bedeutung haben, mit 1 Mol Wasser in Gegenwart einer Base hydrolysiert. c) if X = oxygen, Rl and R2 always together with the common carbon atom of one of the rings mentioned, and d) if Rl and / or Rt are an alkyl radical, at least one of the substituents R3, R4, Rt is different from hydrogen, mean, characterized in that 2 moles of a compound of the formula EMI3.3 wherein Rt, Rt, R3, R4, Rt and X are as defined above, hydrolyzed with 1 mol of water in the presence of a base. II. Die nach dem Verfahren gemäss Patentanspruch 1 herge- stellten Verbindungen. II. The compounds produced by the method according to claim 1. III. Verwendung der Verbindungen gemäss Patentanspruch II zur Herstellung von flammgehemmten polymeren organischen Materialien. III. Use of the compounds according to claim II for the production of flame-retardant polymeric organic materials.
CH131877A 1975-05-16 1975-05-16 Derivs of bis (2-(oxo or thiono)-1,3,2-dioxaphosphorinanyl)oxide CH603674A5 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0475899A1 (en) * 1990-09-12 1992-03-18 Ciba-Geigy Ag Phosphorus compounds
WO2010049083A1 (en) * 2008-10-29 2010-05-06 Lonza Ltd. Process for the production of organic dithiopyrophosphates
US8466096B2 (en) 2007-04-26 2013-06-18 Afton Chemical Corporation 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0475899A1 (en) * 1990-09-12 1992-03-18 Ciba-Geigy Ag Phosphorus compounds
US8466096B2 (en) 2007-04-26 2013-06-18 Afton Chemical Corporation 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions
WO2010049083A1 (en) * 2008-10-29 2010-05-06 Lonza Ltd. Process for the production of organic dithiopyrophosphates
US8324418B2 (en) 2008-10-29 2012-12-04 Lonza Ltd. Process for he production of organic dithiopyrophosphates
EA017760B1 (en) * 2008-10-29 2013-02-28 Лонца Лтд. Process for the production of organic dithiopyrophosphates
TWI427082B (en) * 2008-10-29 2014-02-21 Lonza Ag Process for the production of organic dithiopyrophosphates

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