WO1981000571A1 - Phosphoric acids and their derivatives - Google Patents

Phosphoric acids and their derivatives Download PDF

Info

Publication number
WO1981000571A1
WO1981000571A1 PCT/EP1980/000085 EP8000085W WO8100571A1 WO 1981000571 A1 WO1981000571 A1 WO 1981000571A1 EP 8000085 W EP8000085 W EP 8000085W WO 8100571 A1 WO8100571 A1 WO 8100571A1
Authority
WO
WIPO (PCT)
Prior art keywords
residue
alkyl
atom
alkylene
compounds
Prior art date
Application number
PCT/EP1980/000085
Other languages
German (de)
English (en)
French (fr)
Inventor
M Morr
M Kula
Original Assignee
Biotechnolog Forschung Gmbh
M Morr
M Kula
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19792935134 external-priority patent/DE2935134A1/de
Priority claimed from DE2943016A external-priority patent/DE2943016C2/de
Application filed by Biotechnolog Forschung Gmbh, M Morr, M Kula filed Critical Biotechnolog Forschung Gmbh
Priority to AT80901772T priority Critical patent/ATE13308T1/de
Priority to DE8080901772T priority patent/DE3070645D1/de
Publication of WO1981000571A1 publication Critical patent/WO1981000571A1/de

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
    • 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
    • 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
    • C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
    • 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
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • 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
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/20—Esters of thiophosphoric acids containing P-halide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/52—Cytokines; Lymphokines; Interferons
    • C07K14/555—Interferons [IFN]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon

Definitions

  • the invention relates to compounds of the general formula
  • A oxygen atom
  • X chlorine atom or hydroxyl group
  • Y X or alkoxy radical with 1 to 5 carbon atoms
  • Z oxygen or sulfur atom; or a2)
  • m 1,
  • A oxygen atom
  • X alkoxy radical with 1 to 5 carbon atoms, phenyl alleoxy radical with 0 to 5 carbon atoms in the
  • A oxygen atom
  • X hydroxyl radical
  • Y alkylthio radical with 1 to 5 carbon atoms, aminoalkylthio radical with 2 to 5 carbon atoms or
  • the polyether chain of the above compounds is composed of ethylene glycol, propyleuglycol or 1-propylene glycol units or more of these units; p can have a value of 3 to 250 and preferably 30 to 160.
  • alkoxy radicals are the methoxy, ethoxy and propoxy radical.
  • optionally substituted phenylalfcoxy radicals are optionally substituted alkoxy radicals having 0 to 1 carbon atoms in the alkylene group.
  • alkylamino and dialkylamino residues are the methylamino, ethylamino, propylamino or dirnethylamino, diethylamino and dipropylamino residue.
  • Examples of optionally nucleus-substituted phenylalkylamino and bisphenylalkylamino residues are optionally nucleus-substituted phenylalkylamino or bispheuylalkylamino residues with 0 to 1 carbon atoms in the alkylene group.
  • alkylthio radicals are alkylthio radicals having 1 to 3 carbon atoms.
  • aminoalkylthio radicals are aminoalkylthio radicals having 2 to 3 carbon atoms.
  • Examples of carboxyalkylthio radicals are carboxyalkylthio radicals having 1 to 3 carbon atoms in the alkylene group.
  • An example of a trialkylellyloxy radical is the trimethylsllyloxy radical.
  • the core substituents of the core-substituted phenylalkoxy, phenylalkylamino and bisphenylalkylamino radicals can be a methyl, ethyl, propyl, methoxy, ethoxy and / or propoxy radical.
  • the salts are preferably salts of the acids of phosphorus, preferably ammonium, lithium, sodium or potassium salts.
  • the salts are preferably salts of the acids of phosphorus, preferably ammonium, lithium, sodium or potassium salts.
  • a polyalkylene glycol with phosphorus oxychloride or pyrophosphoryl chloride can be reacted with or without a solvent, such as trialkyl phosphate, for example triethyl phosphate, or dichloromethane, in the presence of an acid scavenger, for example a tertiary base, such as triethylamine or pyridine, or a molecular sieve (with, for example, 0 4 nm).
  • a solvent such as trialkyl phosphate, for example triethyl phosphate, or dichloromethane
  • an acid scavenger for example a tertiary base, such as triethylamine or pyridine, or a molecular sieve (with, for example, 0 4 nm).
  • the phosphoric acid halides obtained can be hydrolyzed with water or first with half the stoichiometric amount of a C 1-5 alcohol and then with water to free phosphoric
  • the free phosphoric acids can also be obtained directly by reaction with a mixture of phosphorus pentoxide and 85% phosphoric acid (condensed phosphoric acids) in the melt.
  • the reaction mixture can be hydrolysed and recrystallized from abs. Ethanol be worked up.
  • Such compounds are obtained if, for example, a polyalkylene glycol is reacted with thiophosphoryl chloride in a solvent, for example in a phos phosphoric acid trialkyl esters, such as triethyl phosphate.
  • the halide obtained can be saponified, for example, at a pH of about 7 in the presence of lithium hydroxide. The free acid can be released in the usual way from the lithium salt.
  • the esters can be obtained by either esterifying the free phosphoric acids obtained according to I) in a conventional manner or by directly reacting the phosphoric acid halides obtained according to I) with alcohols. If the phosphoric acid halides obtained in I) are reacted with amines, the phosphoric acid amides are obtained.
  • the compounds with alkylthio radicals can be obtained, for example, by reacting the compounds obtained according to II) with terminal (LiO) 2 P (S) -O radicals with a trialkyl phosphate in an aqueous medium.
  • the compounds obtained according to II) with an aminoalkyl halide having 2 to 5 carbon atoms or its hydrohalide the compounds with aminoalkylthio are obtained.
  • reaction with a halocarboxylic acid having 1 to 5 carbon atoms in the alkylene chain, for example bromoacetic acid leads to the compounds having carboxyalkylthio radical.
  • the (LiO) 2 P (S) -O radical on the sulfur atom is alkylated.
  • a polyalkylene glycol can be reacted with a thionyl halide, for example thionyl bromide, in a solvent in the presence of an amine, for example in toluene in the presence of triethylamine.
  • a thionyl halide for example thionyl bromide
  • the dihalide obtained with terminal halogen atoms can be reacted in an Akerfeldt reaction to form compounds with (O-) 2 P (O) -S residues, for example with (LiO) 3 PS in a water / DMF mixture.
  • the free acid can be obtained in a known manner from the compound obtained.
  • a polyether obtained in V) with terminal balogen can be obtained Submit atoms to a Michaelis-Arbusov reaction and convert them with a trialkyl phosphate to phosphonic esters.
  • Such esters can also be obtained by a Michaells-Becker reaction in which a polyether having terminal halogen atoms is reacted with alkali metal dialkyl esters, for example sodium phosphorous acid, in a solvent, such as benzene, toluene or an alcohol.
  • the esters obtained can be saponified directly with acids, for example concentrated hydrochloric acid, to give the free phosphonic acids.
  • the free phosphonic acids can also be obtained by first reacting the phosphous acid esters with a trialkylsilyl halide, for example with trimethylsilyl chloride or bromide, and then saponifying with water. This saponification is gentler than acid saponification.
  • a trialkylsilyl halide for example with trimethylsilyl chloride or bromide
  • saponification is gentler than acid saponification.
  • an optionally nucleus-substituted triphenyl phosphite can also be used instead of trialkyl phosphite.
  • Such compounds are obtained if one starts from polyalkylene glycols in which one of the terminal OH radicals is etherified by a C 1-5 alkyl group.
  • the phosphorus-containing polyalkylene glycol derivatives can be used as liquid ion exchangers, for example for the purification of proteins or glycoproteins in two-phase systems. Otherwise, the phosphorus-containing polyalkylene glycol derivatives can be used in the cosmetics, pharmaceuticals and food industries, in particular the esters as crop protection agents and wood preservatives.
  • Example 1 Preparation of bisphosphoric dichloride poly ethylene glycol monoester and bisphosphoric acid polyethylene glycol monoester
  • the intermediate (2) was added by adding 500 ml of water in 2 h Room temperature hydrolyzed. After concentrating in a rotary evaporator, a brown, viscous oil was obtained, which was dissolved in 1 l of water and treated with 20 g of activated carbon (Merck). After filtering, the mixture was concentrated to dryness again, and the residue was dissolved in 1 l of absolute, denatured ethanol. and treated again with 20 g activated carbon.
  • the aqueous solution of compound (3) contained no chloride and no free phosphate.
  • the substance contained no free phosphate and was chloride-free.
  • the compound (3) contained no free thionophosphate and was chloride-free.
  • Polyethylene glycols (molecular weight 1540, 6000, 10000 or 20000) were reacted in toluene in the presence of triethylamine with thiolyl bromide in known catfish; see.

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)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polyethers (AREA)
PCT/EP1980/000085 1979-08-30 1980-08-28 Phosphoric acids and their derivatives WO1981000571A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AT80901772T ATE13308T1 (de) 1979-08-30 1980-08-28 Neue saeuren des phosphors und deren derivate.
DE8080901772T DE3070645D1 (en) 1979-08-30 1980-08-28 Phosphoric acids and their derivatives

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19792935134 DE2935134A1 (de) 1979-08-30 1979-08-30 Neue saeuren des phosphors und deren derivate
DE2935134 1979-08-30
DE2943016A DE2943016C2 (de) 1979-10-24 1979-10-24 Verfahren zur Reinigung von Interferon

Publications (1)

Publication Number Publication Date
WO1981000571A1 true WO1981000571A1 (en) 1981-03-05

Family

ID=25780790

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1980/000085 WO1981000571A1 (en) 1979-08-30 1980-08-28 Phosphoric acids and their derivatives

Country Status (7)

Country Link
US (1) US4416830A (en, 2012)
EP (1) EP0035027B1 (en, 2012)
JP (1) JPS56501092A (en, 2012)
AT (1) ATE13308T1 (en, 2012)
AU (1) AU542509B2 (en, 2012)
DE (1) DE3070645D1 (en, 2012)
WO (1) WO1981000571A1 (en, 2012)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0067694A1 (en) * 1981-06-16 1982-12-22 Dsm Rim Nylon V.O.F Acid halide and acyllactam functional materials and process for the preparation of nylon block polymers therewith
EP0164535A1 (en) * 1981-06-16 1985-12-18 Dsm Rim Nylon V.O.F Acid halide functional materials and process for their preparation
US4628075A (en) * 1981-06-16 1986-12-09 Dsm Rim Nylon Vof Acid halide functional materials
US4645800A (en) * 1981-06-16 1987-02-24 Dsm Rim Nylon Vof Acyllactam functional materials
US4649177A (en) * 1981-06-16 1987-03-10 Dm Rim Nylon Vof Process for the preparation of nylon block polymers
CN106243342A (zh) * 2015-06-03 2016-12-21 信越化学工业株式会社 含有氟代氧化亚烷基的聚合物改性膦酸衍生物及含有其的表面处理剂

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5266722A (en) * 1988-11-09 1993-11-30 W. R. Grace & Co.-Conn. Polyether bis-phosphonic acid compounds
US5017306A (en) * 1988-11-09 1991-05-21 W. R. Grace & Co.-Conn. Corrosion inhibitor
US4981648A (en) * 1988-11-09 1991-01-01 W. R. Grace & Co.-Conn. Inhibiting corrosion in aqueous systems
US4911887A (en) * 1988-11-09 1990-03-27 W. R. Grace & Co.-Conn. Phosphonic acid compounds and the preparation and use thereof
EP0514588B1 (en) * 1991-05-20 1997-06-11 Kao Corporation Novel phosphobetaine and detergent and cosmetic containing the same
US5274101A (en) * 1993-01-07 1993-12-28 Siltech Inc. Polymeric phospholipid polymers
DE19954815C1 (de) * 1999-11-13 2001-06-07 Degussa Verfahren zur Herstellung von schwefel- und phosphorhaltigen Organosiliziumverbindungen
CA2637220C (en) * 2006-02-22 2015-04-21 Tyco Healthcare Group Lp Biodegradable phosphoester polyamines
KR101852521B1 (ko) * 2016-10-14 2018-06-07 에스디코리아(주) 비할로겐 인계 난연제 제조방법

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2314243A1 (fr) * 1975-06-10 1977-01-07 Monsanto Co Fluides hydrauliques a base de composes phosphores
US4154674A (en) * 1976-07-25 1979-05-15 Yeda Research & Development Co., Ltd. Process for removing constituents from a mixture

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2632767A (en) * 1948-12-29 1953-03-24 Standard Oil Dev Co Complex phosphate ester synthetic lubricant
US2853471A (en) * 1955-11-29 1958-09-23 Gen Aniline & Film Corp Making addition polymers and copolymers with phosphorus compound emulsifier
DE1103031B (de) * 1956-07-31 1961-03-23 Hoechst Ag Verfahren zur Herstellung von Polykondensationsprodukten aus endstaendige Hydroxylgruppen aufweisenden Polyaethylenglykolaethern und Sauerstoffsaeuren des Phosphors
US3032578A (en) * 1958-01-06 1962-05-01 Olin Mathieson Phosphonate compositions
NL248754A (en, 2012) 1959-02-24
US3525705A (en) * 1959-04-20 1970-08-25 Mobil Oil Corp Flame-resistant polyurethanes prepared from certain phorphorus compounds
US3277217A (en) * 1963-04-24 1966-10-04 Gen Aniline & Film Corp Process for producing phosphate esters by oxidation of phosphites using hydrogen peroxide and organic peroxides as catalyst
US3340329A (en) * 1963-12-12 1967-09-05 Universal Oil Prod Co Amine salts of oxyalkylenated hydroxyhydrocarbon thiophosphates
DE1447580A1 (de) * 1964-06-19 1968-12-19 Agfa Ag Antistatische photographische Filme
GB1424513A (en) * 1972-06-13 1976-02-11 Ciba Geigy Ag Organic phosphates
JPS5521772B2 (en, 2012) * 1972-09-14 1980-06-12
US4220611A (en) * 1978-06-29 1980-09-02 Sandoz, Inc. Polyoxyalkylene bridged phosphate esters
DE2943016C2 (de) * 1979-10-24 1984-09-06 Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim Verfahren zur Reinigung von Interferon

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2314243A1 (fr) * 1975-06-10 1977-01-07 Monsanto Co Fluides hydrauliques a base de composes phosphores
US4154674A (en) * 1976-07-25 1979-05-15 Yeda Research & Development Co., Ltd. Process for removing constituents from a mixture

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 81, Nr. 22, 02. Dezember 1974 (Columbus, Ohio, US), siehe seite 13, Zusammenfassung 136740w JP, A, 7451400, 18. Mai 1974, Toyobo Co., Ltd. *
Derwent, Band U, Nr. 37, 12. September 1973, siehe Zusammenfassung 54311U JP, B, 7329141, 25. Januar 1969, KAMATA K., et al. *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0067694A1 (en) * 1981-06-16 1982-12-22 Dsm Rim Nylon V.O.F Acid halide and acyllactam functional materials and process for the preparation of nylon block polymers therewith
EP0164535A1 (en) * 1981-06-16 1985-12-18 Dsm Rim Nylon V.O.F Acid halide functional materials and process for their preparation
US4628075A (en) * 1981-06-16 1986-12-09 Dsm Rim Nylon Vof Acid halide functional materials
US4645800A (en) * 1981-06-16 1987-02-24 Dsm Rim Nylon Vof Acyllactam functional materials
US4649177A (en) * 1981-06-16 1987-03-10 Dm Rim Nylon Vof Process for the preparation of nylon block polymers
CN106243342A (zh) * 2015-06-03 2016-12-21 信越化学工业株式会社 含有氟代氧化亚烷基的聚合物改性膦酸衍生物及含有其的表面处理剂
CN106243342B (zh) * 2015-06-03 2020-09-15 信越化学工业株式会社 含有氟代氧化亚烷基的聚合物改性膦酸衍生物及含有其的表面处理剂

Also Published As

Publication number Publication date
EP0035027B1 (de) 1985-05-15
AU6331180A (en) 1981-03-19
JPS56501092A (en, 2012) 1981-08-06
ATE13308T1 (de) 1985-06-15
US4416830A (en) 1983-11-22
AU542509B2 (en) 1985-02-21
EP0035027A1 (de) 1981-09-09
DE3070645D1 (en) 1985-06-20

Similar Documents

Publication Publication Date Title
EP0035027B1 (de) Neue säuren des phosphors und deren derivate
EP0028016B1 (de) Verfahren zur Reinigung von Interferon
DE10153780C1 (de) Verfahren zur Herstellung von Carboxyethylmethylphosphinsäureglykolester und ihre Verwendung
EP1217004B1 (de) Verfahren zur Herstellung von Ethan-1,2-bis(alkylphosphinsäuren)
US3629411A (en) Fungicidal compositions and methods of combating fungi using o-alkyl-s s-dialkyl dithiophosphates
IE48781B1 (en) Fosfomycin derivatives
JPH1045783A (ja) ヒドロキシクロマン誘導体リン酸エステルの製造方法
JP3526940B2 (ja) リン酸エステルの製造法
DE2935134A1 (de) Neue saeuren des phosphors und deren derivate
DE10114352C1 (de) Verfahren zur Herstellung von 1-Hydroxy-1, 1-diphosphonsäureverbindungen
Frank et al. Displacement of tertiary phosphines from methylolphosphonium salts by tributylphosphine
EP0021391B1 (de) Phosphonoameisensäurehydrazide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE19923615C1 (de) Verfahren zur Herstellung von Alkylphosphonigsäureestern
EP0000061B1 (de) Phosphorhaltige Carbonsäure-Derivate, Verfahren zu deren Herstellung, sowie ihre Verwendung
JPH04226997A (ja) アルミニウム−ビス（ヒドロキシメチル）ホスフイネート並びにビス（ヒドロキシメチル）ホスフイネートの製法
DD234274A1 (de) Verfahren zur herstellung nichtionischer und anionischer grenzflaechenaktiver ferrocenderivate
DE68918924T2 (de) Phosphorsäureester.
DE941972C (de) Verfahren zur Herstellung organischer Phosphorverbindungen
DD216465A1 (de) Verfahren zur herstellung substituierter alkanphosphonsaeuren
DE1793466A1 (de) Innere Salze von Estern der Saeuren des Phosphors und deren Herstellung
Ries et al. Synthesis of alkylphosphonates, a new class of antineoplastic agents
SU1209695A1 (ru) Способ получени диарилалкилфосфиноксидов
EP0310559B1 (de) Verfahren zur Herstellung von Alkalimetallsalzen von Phosphonsäuremonoalkylestern
SU596593A1 (ru) Способ получени фосфонопропилцеллюлозы
EP0012194A1 (de) Verfahren zur Herstellung von N-Carboxyalkyl-1-aminoalkan-diphosphonsäuren und Carboxyalkylamino-phenyl-methan-diphosphonsäuren

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 1980901772

Country of ref document: EP

AK Designated states

Designated state(s): AU JP US

AL Designated countries for regional patents

Designated state(s): AT CH DE FR GB LU NL SE

WWP Wipo information: published in national office

Ref document number: 1980901772

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1980901772

Country of ref document: EP