DE1643918A1 - Brominated pentaerythritol phosphates - Google Patents

Brominated pentaerythritol phosphates

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Publication number
DE1643918A1
DE1643918A1 DE19681643918 DE1643918A DE1643918A1 DE 1643918 A1 DE1643918 A1 DE 1643918A1 DE 19681643918 DE19681643918 DE 19681643918 DE 1643918 A DE1643918 A DE 1643918A DE 1643918 A1 DE1643918 A1 DE 1643918A1
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Prior art keywords
phosphate
oxetane
formula
alcohol
phosphates
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Pending
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DE19681643918
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German (de)
Inventor
Carl Moore
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Dow Chemical Co
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Dow Chemical Co
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Publication of DE1643918A1 publication Critical patent/DE1643918A1/en
Pending legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
    • 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
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/18—Fireproof paints including high temperature resistant paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/10—Phosphorus-containing compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/34—Ignifugeants
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K2200/00—Wooden materials to be treated
    • B27K2200/10—Articles made of particles or fibres consisting of wood or other lignocellulosic material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K2240/00—Purpose of the treatment
    • B27K2240/30—Fireproofing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/16—Inorganic impregnating agents
    • B27K3/166—Compounds of phosphorus
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/50—Mixtures of different organic impregnating agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

Patentanwälte Dipl.-Ing. R Weickmann, Dr. Ing. A. WeickmannPatent attorneys Dipl.-Ing. R Weickmann, Dr. Ing.A. Weickmann

Dipl.-Ing. H. Weickmann» Dipl-Phys. Dr. K. Fincke HMY D1PL.-ING. F. A.Weickmann, Dipl.-Chem. B. HuberDipl.-Ing. H. Weickmann »Dipl-Phys. Dr. K. Fincke HMY D1PL.-ING. F. A. Weickmann, Dipl.-Chem. B. Huber

8 MÜNCHEN 27, DEN Gase 12 342-ί1 MÖHLSTRASSE 22, RUFNUMMER 483921/228 MÜNCHEN 27, DEN Gase 12 342-ί 1 MÖHLSTRASSE 22, CALL NUMBER 483921/22

THE DOW CHEMICAL COMPANY", Midland, Michigan / V. Sta. A.THE DOW CHEMICAL COMPANY ", Midland, Michigan / V. Sta. A.

ßromierte PentaerythritphosphateChromated pentaerythritol phosphates

Die Erfindung betrifft neue Phosphatester und ihre Verwendung als Zusatzstoffe zur Schaffung von Flammfestigkeit "bei verbrennbaren Materialien.The invention relates to new phosphate esters and their use as additives to provide flame resistance "with combustible materials.

Es wurden bereits viele bromhaltige Verbindungen
ale Zusatzstoffe zur Erhöhung der Widerstandsfähigkeit gegen Brennen von verbrennbaren Stoffen wie Kunststoffen, Holz, Papier und Cellulosefasern verwendet. Auch Phosphate, sowohl organische als auch anorganische, wurden zu diesem Zweck bereits verwendet einschließlich von Phosphaten einiger bro-There have been many bromine-containing compounds
All additives are used to increase the resistance to burning of combustible materials such as plastics, wood, paper and cellulose fibers. Phosphates, both organic and inorganic, have also been used for this purpose, including phosphates from some bro-

109831/2153109831/2153

mierter Alkohole und Phenole. Obwohl diese bekannten Phosphate wirksam sind, -wurden sie als brennverzögernde Zusatzmittel nicht in weitem Umfange und auch nicht in solcher Menge verwendet, daß nicht weiter ein Bedarf nach einer besseren Beständigmachung von verbrennbaren Stoffen gegen Brennen bestanden hätte, weitgehend infolge bestimmter Nachteile, die den meisten bisher bekannten derartigen Verbindungen anhaften. Bromierte organische Phosphate beispielsweise besitzen oft nicht ausreichende 'Widerstandsfähigkeit gegen Zersetzung durch tfärme, Licht, Feuchtigkeit oder Kombinationen davon und verursachen daher Verfärbung, Verschlechterung der Festigkeit oder anderer physikalischer Eigenschaften oder Abgabe saurer .Nebenprodukte durch die Orundstoffe, in denen sie entnalten sind. Bekannte bromierte organische Phosphate können mit dem Substrat auch ungenügend verträglich sain, so daß 3ie nicüit in wirKsamen mengen verwendet werden können.mated alcohols and phenols. Although these are known phosphates Are effective, they were not widely used as flame retardant additives and not even in such a way Amount used that there is no further need for a better resistance to combustible materials Burning would have persisted, largely as a result of certain disadvantages common to most of the heretofore known such compounds cling. Brominated organic phosphates, for example, often have insufficient resistance against decomposition due to heat, light, moisture or combinations of it and therefore cause discoloration, deterioration the strength or other physical properties or the release of acidic by-products through the substances, in which they are deprived. Well known brominated organic Phosphates can also be insufficiently compatible with the substrate, so that they are not used in effective quantities can be.

Nunmehr wurde gefunden, daß bromierte organische o-Phosphate spezieller Struktur nicht nur äußerst wirksame Flammverzögerungszusätze für Kunststoffe und Gellulosebasismaterialien darstellen, sondern daß diese Verbindungen auchIt has now been found that brominated organic o-phosphates with a special structure are not only extremely effective Flame retardant additives for plastics and cellulose base materials represent, but that these connections too

10 9831/2153 ßAD 10 9831/2153 ßAD

ungewöhnliche und unerwartete thermische, hydrolytische und püotolytische Stabilität aufweisen. Diese neuen Verbindungen sind die Phosphate eines polybromierten Pentaerythrits der Formel Ihave unusual and unexpected thermal, hydrolytic and piotolytic stability. These new connections are the phosphates of a polybrominated pentaerythritol of the formula I.

BrCH0 -BrCH 0 -

C - GH2OH GH2XC - GH 2 OH GH 2 X

worin X *-Ίι1ογ oder Brom ist. Die Erfindung betrifft speziell die Triester der Formel IIwherein X * is -Ίι1ογ or bromine. The invention particularly relates the Trieste of Formula II

CH2BrCH 2 Br

BrGH2 - C - CH2 - 0 , CH2XBrGH 2 - C - CH 2 - 0 CH 2 X

POPO

IIII

worin X die obige Bedeutung besitzt. Die Triester der Phosphorsäure, worin X Brom ist, werden bevorzugt.wherein X has the above meaning. The triesters of phosphoric acid, where X is bromine are preferred.

Wie angegeben, sind die Phosphatester der Erfindung äußerst wirksame Flammversögerungsmittel, insbesondere in Ge-As indicated, the phosphate esters of the invention are extremely effective flame retardants, especially in areas

109831/2153109831/2153

BADBATH

genwart von Triphenylphosphat oder einem freie Radikale erzeugenden Stoff, von dem bekannt ist, daß er die Peuerlöschungswirksamkeit halogenierter organischer Verbindungen fördert. Die erfindungsgemäßen Ester lassen sich bequem herstälen, indem der Alkohol oder 3,3-Bis-(brommethyl)-oxetan mit Phosphoroxychlorid oder-oxybromid in Berührung gebracht wird, vorzugsweise in Gegenwart eines Lösungsmittels für die Reagentien, und der Ester nach an sich bekannten Methoden gewonnen wird.presence of triphenyl phosphate or a free radical generator Substance known to have the extinguishing effectiveness of halogenated organic compounds promotes. The esters according to the invention can be conveniently prepared by adding the alcohol or 3,3-bis (bromomethyl) oxetane is brought into contact with phosphorus oxychloride or oxybromide, preferably in the presence of a solvent for the Reagents, and the ester according to methods known per se is won.

Die durch die obige Formel I wiedergegebenen Alkohole sind bekannt und werden gewöhnlich durch Umsetzung von Pentaerythrit mit Phoephortribromid oder ähnlichen Bromierungsmitteln hergestellt. Die Phosphatester lassen sich.bequem herstellen durch Umsetzung des bromierten Alkohols oder Derivates davon mit Phosphoroxychlorid, wie die Beispiele zeigen.The alcohols represented by the above formula I are known and are usually obtained by reacting Pentaerythritol with phosphorus tribromide or similar brominating agents manufactured. The phosphate esters can be conveniently prepared by reacting the brominated alcohol or Derivatives thereof with phosphorus oxychloride, as the examples show.

B e i β ρ ie 1B e i β ρ ie 1 11

Eine Mischung von 325 g 3-Brom-2,2-bis-(brommethyl)-1-propanol, 82 g Pyridin und 500 ml Perchloräthylen wurde in einem 1 1-Kolben hergestellt. Der gerührten Mischung wurdenA mixture of 325 g of 3-bromo-2,2-bis (bromomethyl) -1-propanol, 82 g of pyridine and 500 ml of perchlorethylene were prepared in a 1 liter flask. The stirred mixture were

109831/2153109831/2153

dann 54,2 g Phosphoroxyohlorid (POGl^) innerhalb von 15 Minuten zugegeben. Die erhaltene Reaktionsmischung wurde gerührt und 1 1/2 Stunden auf 1200O erhitzt. Dann wurde die Mischung abgekühlt und in 1 1 kaltes Wasser gegossen, worauf ein voluminöser weißer Feststoff sich in der wässrigen Phase absetzte. Der Peststoff wurde abfiltriert, gewaschen und getrocknet, wobei 103 g Tris-(3-brom-2,2-bis-(brommethyl)-propyl)-phosphat, F. = 172 bis 1730C, erkalten wurde. Die Blementaranalyse und infrarotspektroskopische Untersuchung bestätigten die Identität des Produktes.then 54.2 g of phosphorus oxychloride (POGl ^) added within 15 minutes. The reaction mixture was stirred and heated for 1 1/2 hours at 120 0 O. The mixture was then cooled and poured into 1 liter of cold water, whereupon a voluminous white solid settled in the aqueous phase. The Peststoff was filtered, washed and dried to obtain 103 g of tris (3-bromo-2,2-bis (bromomethyl) propyl) phosphate, mp = 172-173 0 C was, to cool. The elemental analysis and infrared spectroscopic examination confirmed the identity of the product.

Beispiel 2 Example 2

Eine Lösung von 122 g 3,3-Bis-(brommethyl)-oxetan in 200 ml Perchloräthylen wurde in einem Reaktionskolben hergestellt. Dieser Lösung wurden innerhalb von 30 Minuten 27,5 g Phosphoroxyohlorid zugesetzt. Die Reaktionsmischung wurde insgesamt 30 Stunden bei 60 bis 1700C gerührt unter Zusatz von 0,3 g Magnesiumchlorid nach 2 Stunden und von 0,5 g Aluminiurachlorid nach 22 Stunden. Dann wurde die Reaktionsmischung gekühlt, mit Wasser gewaschen, filtriert, das Lösungsmittel au3 der organischen Schicht abgestreift und der Rückstand aus Benzol umkristallisiert, wobei 116 g eineeA solution of 122 g of 3,3-bis (bromomethyl) oxetane in 200 ml of perchlorethylene was prepared in a reaction flask. 27.5 g of phosphorus oxychloride were added to this solution over a period of 30 minutes. The reaction mixture was stirred for a total of 30 hours at 60 to 170 ° C. with the addition of 0.3 g of magnesium chloride after 2 hours and of 0.5 g of aluminum chloride after 22 hours. The reaction mixture was then cooled, washed with water, filtered, the solvent stripped from the organic layer, and the residue recrystallized from benzene to give 116 g of ae

109831 /2153109831/2153

feinen weißen Pulvers vom J?. = 1650C erhalten wurden. Elementaranalyse und infrarotspektroskopische Untersuchung ergaben, daß es sich hierbei um das erwartete Tris-(3-brom-2-brommethyl-2-chloEJnethylpropyl)-phosphat handelte.fine white powder from J ?. = 165 0 C were obtained. Elemental analysis and examination by infrared spectroscopy showed that this was the expected tris (3-bromo-2-bromomethyl-2-chloro-methylpropyl) phosphate.

Die Phosphate der Erfindung sind wirksame Zusatzmittel bei der Herstellung von selbstlöschenden Harzen, wenn sie alkeny!aromatischen Polymerisaten wie Polystyrol in Konzentrationen in der Größenordnung von 2 Gew.fe einverleibt werden. Sie werden in diesen Harzen vorzugsweise in Kombination mit einem synergistischen Zusatzaiittel wie Tri— phenylphosphat oder einem freiradikalieehen Initiator verwendet, von dem bekannt ist, daß er die üelbstlöschungsaktivität halogenierter organischer Verbindungen steigert. Infolge der einmaligen Widerstandsfähigkeit dieser Verbindungen gegen thermische, hydrolytische und photolytische Zersetzung, können diese enthaltende Harze geformt bzw. preßgeformt werden, ohne merkliche Korrosion der Metallteile,und die geformten Harze weisen eine große Widerstandsfähigkeit gegen Vergilben und Verschlechterung anderer Eigenschaften auf.The phosphates of the invention are effective additives in the manufacture of self-extinguishing resins when incorporated into alkenyl aromatic polymers such as polystyrene in concentrations on the order of 2 percent by weight. They are preferably used in these resins in combination with a synergistic additive such as triphenyl phosphate or a free radical initiator which is known to increase the self-extinguishing activity of halogenated organic compounds. Due to the exceptional resistance of these compounds against thermal, hydrolytic and photolytic decomposition, containing these resins may be formed or press-formed, without any significant corrosion of the metal parts and the molded resins have a high resistance to yellowing and deterioration of other properties.

1 C) '3 s 11/21531 C) '3 s 11/2153

Aus den _gleiclien Gründen sind diese neuen Verbindungen wirksame und wertvolle Zusatziuittel zur Erhöhung der Feuerbeständigkeit von Cellulosematerialien wie Holzf Papier und Gellulosefasern, wenn sie auf diesen nach üblichen Methoden angewandt werden. Infolge ihrer Wirksamkeit für diesen Zxeck müssen nur minimale Mengen,dieser Phosphate verwendet ¥er3en,uiid die Faserfestigkeit und andere Eigenschaften des Gellulosesubstrates werden nicht merklich beeinträchtigt.From the _gleiclien reasons, these new compounds are potent and valuable Zusatziuittel to increase the fire resistance of cellulose materials wood f paper and cellulose fibers when they are applied to these by conventional methods such. As a result of their effectiveness for this purpose, only minimal amounts of these phosphates have to be used, and the fiber strength and other properties of the gelulose substrate are not noticeably impaired.

BAD 109831/2153 BATH 109831/2153

Claims (4)

ERt-CHBERt-CHB 1. Phosphatester eines Alkohols der Formel I1. Phosphate ester of an alcohol of the formula I. BrCH^ -BrCH ^ - CH2BrCH 2 Br C - CH2OHC - CH 2 OH CH2XCH 2 X worin X Chlor oder Brom ist.wherein X is chlorine or bromine. 2. Phosphatester der Formel II2. Phosphate ester of the formula II BrCHo -BrCHo - CH2Br C - CH2 CH2XCH 2 Br C - CH 2 CH 2 X - O- O PO IIPO II worin X Chlor oder Brom ist.wherein X is chlorine or bromine. 3. Flammverzögerunggmittel, dadurch gekennzeichnet, daß es im wesentlichen aus dem Phosphatester von Anspruch oder 2 besteht. -3. Flame retardant, characterized in that that it consists essentially of the phosphate ester of claim or 2. - 109831/2153109831/2153 BADBATH 4. Flammveraögerungsmittel nach Anspruch 3, dadurch' gekennzeichnet, daß es außerdem Tripheny!phosphat oder einen freie Radikale "bildenden Stoff enthält, von dem bekannt ist, daß er die Feuerlöschaktivität halogenierter organi-.scher Verbindungen verbessert.4. Flammvera retardant according to claim 3, characterized ' characterized that it also tripheny! phosphate or a contains free radical forming substance known from the is that it can reduce the fire extinguishing activity of halogenated organic Connections improved. 5» Verfahren zur Herstellung von Phosphatestern durch Zusammenbringen eines Alkohols oder Oxetane mit Phosphoroxychlorid oder Phosphoroxybromid, wanlweise in Gegenwart eines Lösungsmittels für die Reagentien, dadurch gekennzeichnet, daß ein Alkohol der Formel I verwendet und als Oxetan 3τ3-Bis-(brommethyl)-oxetan verwendet wird. " .5 »Process for the preparation of phosphate esters by combining an alcohol or oxetane with phosphorus oxychloride or phosphorus oxybromide, sometimes in the presence of one Solvent for the reagents, characterized in that an alcohol of the formula I is used and the oxetane is 3τ3-bis (bromomethyl) oxetane is used. ". 6ο Phosphatester, dadurch gekennzeic}inet, daß sie nach dein Verfahren von Anspruch 5 erhalten wurden.6ο phosphate esters, characterized in that they according to the method of claim 5. 109831/2153109831/2153 BADBATH
DE19681643918 1967-01-16 1968-01-12 Brominated pentaerythritol phosphates Pending DE1643918A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
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BE (1) BE709417A (en)
DE (1) DE1643918A1 (en)
FR (1) FR1556439A (en)
GB (1) GB1173252A (en)
NL (1) NL6800609A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1090058A (en) * 1976-12-09 1980-11-25 Ray E. Smith Flame retardant finishes for textile materials
US4714771A (en) * 1985-11-27 1987-12-22 The Dow Chemical Company Process for preparing halogenated trialkyl phosphate esters

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BE709417A (en) 1968-07-16
FR1556439A (en) 1969-02-07
GB1173252A (en) 1969-12-03

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