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DE1148969B - Procedure for flame retardant equipment - Google Patents

Procedure for flame retardant equipment

Info

Publication number
DE1148969B
DE1148969B DEF22591A DEF0022591A DE1148969B DE 1148969 B DE1148969 B DE 1148969B DE F22591 A DEF22591 A DE F22591A DE F0022591 A DEF0022591 A DE F0022591A DE 1148969 B DE1148969 B DE 1148969B
Authority
DE
Germany
Prior art keywords
seconds
flame retardant
procedure
optionally substituted
substituted hydrocarbon
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.)
Pending
Application number
DEF22591A
Other languages
German (de)
Inventor
Dr Fritz Kassack
Dr Friedrich Lober
Dr Hugo Malz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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 to CH120357D priority Critical patent/CH120357A/en
Priority to DEP477A priority patent/DE832004C/en
Priority to CH291056D priority patent/CH291056A/en
Priority to DEF20264A priority patent/DE1087109B/en
Priority to DEF20584A priority patent/DE1021526B/en
Priority to DEP16486A priority patent/DE1137619B/en
Priority to CH355291D priority patent/CH355291A/en
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF22591A priority patent/DE1148969B/en
Priority to DEF21526A priority patent/DE1025086B/en
Priority to CH351825D priority patent/CH351825A/en
Priority to FR1160553D priority patent/FR1160553A/en
Priority to US640035A priority patent/US2977913A/en
Priority to CH359134D priority patent/CH359134A/en
Priority to FR1177733D priority patent/FR1177733A/en
Priority to GB11039/57A priority patent/GB830800A/en
Priority to CH355316D priority patent/CH355316A/en
Priority to FR1174947D priority patent/FR1174947A/en
Priority to GB16236/57A priority patent/GB813733A/en
Publication of DE1148969B publication Critical patent/DE1148969B/en
Pending legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04L—TRANSMISSION OF DIGITAL INFORMATION, e.g. TELEGRAPHIC COMMUNICATION
    • H04L21/00—Apparatus or local circuits for mosaic printer telegraph systems
    • H04L21/02—Apparatus or local circuits for mosaic printer telegraph systems at the transmitting end
    • 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
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/224—Phosphorus triamides
    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/564—Three-membered rings
    • 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
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/6533—Six-membered rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/16—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-nitrogen bond
    • D—TEXTILES; PAPER
    • D05—SEWING; EMBROIDERING; TUFTING
    • D05B—SEWING
    • D05B29/00—Pressers; Presser feet
    • D—TEXTILES; PAPER
    • D05—SEWING; EMBROIDERING; TUFTING
    • D05B—SEWING
    • D05B29/00—Pressers; Presser feet
    • D05B29/06—Presser feet
    • 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
    • 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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01P—MEASURING LINEAR OR ANGULAR SPEED, ACCELERATION, DECELERATION, OR SHOCK; INDICATING PRESENCE, ABSENCE, OR DIRECTION, OF MOVEMENT
    • G01P1/00—Details of instruments
    • G01P1/12—Recording devices
    • G01P1/122—Speed recorders
    • G01P1/125—Speed recorders with recording discs
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/049—Phosphite
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Computer Networks & Wireless Communication (AREA)
  • Signal Processing (AREA)
  • Lubricants (AREA)
  • Fireproofing Substances (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Lock And Its Accessories (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

F 22591IVc/8kF 22591IVc / 8k

ANMELDETAG: 18. MARZ 1957REGISTRATION DATE: MARCH 18, 1957

BEKANNTMACHUNG
DER ANMELDUNG
UNDAUSGABE DER
AUSLEGESCHRIFT: 22. MAI 1963 NOTICE
THE REGISTRATION
AND ISSUE OF
EDITORIAL: MAY 22, 1963

Gegenstand der Patentanmeldung F 20264 IVc/8 k (deutsche Auslegeschrift 1 087 109) ist ein Verfahren zur Flammschutz-Ausrüstung, welches darin besteht, daß man die hierfür in Betracht kommenden brennbaren Materialien mit Lösungen oder Dispersionen von N-mono- oder N-disubstituierten Amidophosphorsäureverbindungen der allgemeinen FormelSubject of patent application F 20264 IVc / 8 k (German Auslegeschrift 1 087 109) is a method for flame protection equipment, which consists in that the combustible materials which are suitable for this purpose are mixed with solutions or dispersions of N-mono- or N-disubstituted amidophosphoric acid compounds the general formula

H2N-H 2 N-

-P-NH--P-NH-

Verfahren zur Flammschutz-AusrüstungProcess for flame retardant finishing

Zusatz zur Patentanmeldung F 20264 IVc/8 k
(Auslegeschrift 1 087 109)Addition to patent application F 20264 IVc / 8 k
(Auslegeschrift 1 087 109)

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft,
LeverkusenPaint factories Bayer Aktiengesellschaft,
Leverkusen

in der X einen gegebenenfalls substituierten Kohlenwasserstoffrest und Y Wasserstoff oder ebenfalls einen gegebenenfalls substituiertenKohlenwasserstoffrest bedeutet oder in der X und Y zusammen mit dem Stickstoffatom einen heterocyclischen Rest bilden, während η = 1 oder eine andere ganze Zahl bedeutet, imprägniert und dann einer Nacherhitzung unterwirft.in which X is an optionally substituted hydrocarbon radical and Y is hydrogen or likewise an optionally substituted hydrocarbon radical, or in which X and Y together with the nitrogen atom form a heterocyclic radical, while η = 1 or another integer, impregnated and then subjected to reheating.

Gegenstand der Erfindung ist nun eine Änderung dieses Verfahrens; sie besteht darin, daß man die entsprechenden Verbindungen, in denen der Sauerstoff durch Schwefel ersetzt ist, verwendet.The subject of the invention is now a change in this method; it consists in having the corresponding compounds in which the oxygen is replaced by sulfur is used.

Als Kohlenwasserstoffreste kommen wie bei den Verfahren der Hauptpatentanmeldung gesättigte oder ungesättigte Alkyl-, Cycloalkyl-, Aryl- und Aralkylreste in Betracht; geeignete heterocyclische Reste sind beispielsweise der Pyrrolidin-, der Piperidin-, der Hexymethylenimin- und der Morpholinrest.As in the processes of the main patent application, saturated or saturated hydrocarbon radicals are used Unsaturated alkyl, cycloalkyl, aryl and aralkyl radicals are suitable; suitable heterocyclic radicals are for example the pyrrolidine, the piperidine, the hexymethyleneimine and the morpholine radical.

Die erfindungsgemäß als Flammschutzmittel zu verwendenden Verbindungen können in mannigfacher Weise hergestellt sein, beispielsweise durch Umsetzung von N-mono- oder N-disubstituierten Amidothiophosphorsäuredichloriden mit Ammoniak.The compounds to be used according to the invention as flame retardants can be used in manifold Wise prepared, for example by reacting N-mono- or N-disubstituted Amidothiophosphoric acid dichlorides with ammonia.

Mit Hilfe des erfindungsgemäßen Verfahrens gelingt es, den verschiedenartigsten Materialien, wie z. B. Holz, Pappe, Leder und Kunststoffen, vor allem aber Textilien einen wirksamen Flamm- und Glimmschutz zu verleihen. Die Anwendung der Amidothiophosphorsäureverbindungen kann in an sich bekannter Weise erfolgen, z. B. in Form von Lösungen in geeigneten Lösungsmitteln, wie z. B. in Wasser, Alkoholen, Estern, Kohlenwasserstoffen bzw. halogenierten Kohlenwasserstoffen, oder auch in Form von Dispersionen.With the help of the method according to the invention it is possible to use a wide variety of materials, such as z. B. wood, cardboard, leather and plastics, but especially textiles an effective flame and corona protection to rent. The use of the amidothiophosphoric acid compounds can be known per se Be done, e.g. B. in the form of solutions in suitable solvents, such as. B. in water, Alcohols, esters, hydrocarbons or halogenated hydrocarbons, or in the form of dispersions.

Man kann die Amidothiophosphorsäureverbindungen auch zusammen mit mono- oder poly-Dr. Hugo Malz, Leverkusen, Dr. Fritz Kassack,
Köln-Stammheim,The amidothiophosphoric acid compounds can also be used together with mono- or poly-Dr. Hugo Malz, Leverkusen, Dr. Fritz Kassack,
Cologne-Stammheim,

und Dr. Friedrich Lober, Leverkusen-Bayerwerk,
sind als Erfinder genannt wordenand Dr. Friedrich Lober, Leverkusen-Bayerwerk,
have been named as inventors

funktionellen Isocyanaten oder mit Kondensationsprodukten aus Formaldehyd und Harnstoff, Guanidin, Dicyandiamid bzw. Melamin oder mit anderen, vernetzend wirkenden Verbindungen einsetzen; man erhält dann Flammfestausrüstungen, die sich durch eine besondere Beständigkeit auszeichnen. So besitzen z. B. Textilien, die auf diese Weise behandelt sind, eine Flamm- und Glimmschutzausrüstung von überraschend hoher Beständigkeit gegenüber Kochwäschen sowie gegenüber Benzin- oder Perchloräthylenwäschen. functional isocyanates or with condensation products of formaldehyde and urea, guanidine, Use dicyandiamide or melamine or with other, crosslinking compounds; man then receives flame-retardant finishes, which are characterized by a special resistance. So own z. B. Textiles that are treated in this way, a flame and corona protection finish from Surprisingly high resistance to hot washes and to petrol or perchlorethylene washes.

Es ist bereits vorgeschlagen worden, Umsetzungsprodukte von Phosphorthiochlorid und Ammoniak, also Amidothiophosphorsäureverbindungen in der Art des Thiophosphorsäuretriamids, zur Flamm- und Glimmschutzausrüstung zu verwenden; diese Mittel unterliegen jedoch im allgemeinen leicht der Hydrolyse und werden dadurch unwirksam. Die erfindungsgemäß zu verwendenden Mittel besitzen diesen Nachteil nicht.It has already been proposed to use reaction products of phosphorothiochloride and ammonia, So amidothiophosphoric acid compounds in the type of thiophosphoric acid triamide, for flame and To use corona protection equipment; however, these agents are generally susceptible to hydrolysis and thereby become ineffective. The agents to be used according to the invention have this Disadvantage not.

Die in den Beispielen angegebenen Teile sind Gewichtsteile.The parts given in the examples are parts by weight.

Beispiel 1example 1

Ein Baumwollgewebe vom Gewicht 225 g/m2 wurde auf dem Foulard mit einer Lösung aus 15 Teilen N-Diäthylamidothiophosphorsäurediamid, 80 Teilen Aceton und 5 Teilen Wasser getränkt, anschließend auf eine Gewichtszunahme von 75% abgequetscht, bei 60° C getrocknet und 10 Minuten auf 1500C erhitzt.A cotton fabric weighing 225 g / m 2 was impregnated on a padder with a solution of 15 parts of N-diethylamidothiophosphoric acid diamide, 80 parts of acetone and 5 parts of water, then squeezed off to a weight increase of 75%, dried at 60 ° C. and followed for 10 minutes 150 0 C heated.

309 597/308309 597/308

Die Flammfestprüfung des so behandelten Gewebes, die nach den in den Deutschen Normen (DIN 53 906, Entwurf vom Juli 1955) beschriebenen Richtlinien für die Prüfung schwerentflammbar ausgerüsteter Textilien bei senkrecht aufgespannten Proben vorgenommen wurde, ergab folgende Werte:The flame resistance test of the fabric treated in this way, which is carried out in accordance with the German standards (DIN 53 906, draft of July 1955) described guidelines for testing flame retardant equipment Textiles with vertically stretched samples resulted in the following values:

Beispiel 3Example 3

Behandeltes' GewebeTreated 'tissue

Kochwäsche Whites

Benzinwäsche Petrol washing

BrenntestBurn test

0 Sekunden
2 Sekunden
0 Sekunden0 seconds
2 seconds
0 seconds

GlimmtestGlow test

0 Sekunden 0 Sekunden 0 Sekunden Ein Baumwollgewebe der im Beispiel 1 genannten Art wurde auf dem Foulard mit einer Lösung aus Teilen N-Dimethylamidothiophosphorsäurediamid und 80 Teilen Wasser getränkt. Anschließend wurde das Gewebe auf eine Gewichtszunahme von 91% abgequetscht, bei 85°C getrocknet und 10 Minuten auf 1500C erhitzt.0 seconds 0 seconds 0 seconds A cotton fabric of the type mentioned in Example 1 was impregnated on a padder with a solution of parts of N-dimethylamidothiophosphoric acid diamide and 80 parts of water. Subsequently, the fabric was squeezed to a weight gain of 91%, dried at 85 ° C and heated for 10 minutes 150 0 C.

Die gemäß Beispiel 1 durchgeführte Flammfestprüfung ergab folgende Werte:The flame resistance test carried out according to Example 1 gave the following values:

N-Diäthylamidothiothiophosphorwar in folgender Weise hergestelltN-diethylamidothiophosphorus was prepared in the following manner

Das benutzte
säurediamid
worden:That used
acid diamide
been:

In eine Lösung von 175 ml Diäthylamidothiophosphorsäuredichlorid in 11 Methylenchlorid wurde bei Raumtemperatur unter Rühren trockenes Ammoniakgas bis zur Sättigung eingeleitet. Der bei der Reaktion gebildete weiße Niederschlag, der zum überwiegenden Teil aus Ammoniumchlorid bestand, wurde abfiltriert, das klare farblose Filtrat wurde im Vakuum auf etwa ein Viertel eines Volumens eingeengt und anschließend mit einer Eis-Kochsalz-Mischung gekühlt. Aus der gekühlten Lösung schied sich das Diamid der Diäthylamidothiophosphorsäure in einer Ausbeute von etwa 70% in Form farbloser Kristalle ab, die nach Umkristallisieren aus Tetrachlorkohlenstoff einen Schmelzpunkt von 63 bis 64° C zeigten.In a solution of 175 ml of diethylamidothiophosphoric acid dichloride in 11 methylene chloride was dry ammonia gas with stirring at room temperature initiated until saturation. The white precipitate formed in the reaction, the predominantly consisted of ammonium chloride, was filtered off, the clear, colorless filtrate was im Vacuum reduced to about a quarter of a volume and then with an ice and salt mixture chilled. The diamide of diethylamidothiophosphoric acid separated out from the cooled solution in a yield of about 70% in the form of colorless crystals, which after recrystallization from carbon tetrachloride showed a melting point of 63 to 64 ° C.

Beispiel 2Example 2

Ein Baumwollgewebe der im Beispiel 1 genannten Art wurde in der dort angegebenen Weise mit einer Lösung behandelt, die 15 Teile N-Diäthylamidothiophosphorsäurediamid, 15 Teile eines wasserlöslichen handelsüblichen Melamin-Formaldehyd-Vorkondensats und 70 Teile Aceton enthielt. Anschließend wurde das Gewebe auf eine Gewichtszunahme von 75% abgequetscht, bei 6O0C getrocknet und 10 Minuten auf 150°C erhitzt.A cotton fabric of the type mentioned in Example 1 was treated in the manner indicated there with a solution which contained 15 parts of N-diethylamidothiophosphoric acid diamide, 15 parts of a water-soluble commercial melamine-formaldehyde precondensate and 70 parts of acetone. Subsequently, the fabric was squeezed to a weight gain of 75%, dried at 6O 0 C and heated for 10 minutes 150 ° C.

Die gemäß Beispiel 1 durchgeführte Flammfestprüfung ergab folgende Werte:The flame resistance test carried out according to Example 1 gave the following values:

Behandeltes Gewebe,Treated tissue,

Kochwäsche Whites

Benzinwäsche ,Petrol washing,

BrenntestBurn test

0 Sekunden0 seconds

0,5 Sekunden0.5 seconds

0 Sekunden0 seconds

GlimmtestGlow test

0 Sekunden 0 Sekunden 0 Sekunden0 seconds 0 seconds 0 seconds

Behandeltes GewebeTreated tissue

Kochwäsche Whites

Benzinwäsche Petrol washing

BrenntestBurn test

0 Sekunden
2 Sekunden
0 Sekunden0 seconds
2 seconds
0 seconds

GlimmtestGlow test

0 Sekunden
0 Sekunden
0 Sekunden Das eingesetzte N-Dimethylamidothiophosphorsäurediamid war durch Einwirkung von Ammoniak auf N - Dimethylamidothiophosphorsäuredichlorid hergestellt worden.0 seconds
0 seconds
0 seconds The N-dimethylamidothiophosphoric acid diamide used was produced by the action of ammonia on N-dimethylamidothiophosphoric acid dichloride.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Änderung des Verfahrens zur Flammschutzausrüstung gemäß Patentanmeldung F 20264 IVc/ 8 k, (deutsche Auslegeschrift 1087109), bei welchem die hierfür in Betracht kommenden brennbaren Materialien mit Lösungen oder Dispersionen von N-mono- oder N-disubstituierten Amidophosphorsäureverbindungen der allgemeinen FormelChange of the procedure for flame retardant finishing according to patent application F 20264 IVc / 8 k, (German Auslegeschrift 1087109), at which the flammable materials in question with solutions or Dispersions of N-mono- or N-disubstituted amidophosphoric acid compounds of the general formula 35 H2N35 H 2 N P-NHP-NH \
Y\
Y in der X einen gegebenenfalls substituierten Kohlenwasserstoffrest und Y Wasserstoff oder ebenfalls einen gegebenenfalls substituierten Kohlenwasserstoffrest bedeutet oder in der X und Y zusammen mit dem Stickstoffatom einen heterocyclischen Rest bilden, während η 1 oder eine andere ganze Zahl bedeutet,, imprägniert und dann einer Nacherhitzung unterworfen werden, dadurch gekennzeichnet, daß man hier die entsprechenden Verbindungen, in denen der Sauerstoff durch Schwefel ersetzt ist, verwendet.in which X is an optionally substituted hydrocarbon radical and Y is hydrogen or likewise an optionally substituted hydrocarbon radical, or in which X and Y together with the nitrogen atom form a heterocyclic radical, while η means 1 or another integer, impregnated and then subjected to post-heating , characterized in that the corresponding compounds in which the oxygen is replaced by sulfur are used here. In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr. 831 538.Documents considered: German Patent No. 831 538. ® 309 597/308 S. ® 309 597/308 S.
DEF22591A 1948-11-13 1956-10-29 Procedure for flame retardant equipment Pending DE1148969B (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
CH120357D CH120357A (en) 1956-04-05 1926-03-26 Electromagnetic self-switch, especially in the form of a plug.
DEP477A DE832004C (en) 1948-11-13 1948-11-13 Arrangement for the optional delivery of different pulse sequences, especially for teleprinters
CH291056D CH291056A (en) 1956-04-05 1950-12-22 Arrangement for the optional delivery of different pulse sequences, especially for teleprinters.
DEF20264A DE1087109B (en) 1956-04-05 1956-04-05 Procedure for flame retardant equipment
DEF20584A DE1021526B (en) 1956-04-05 1956-05-11 Lubricant additives
DEP16486A DE1137619B (en) 1956-04-05 1956-06-20 Fabric presser foot for making buttonholes
CH355291D CH355291A (en) 1955-12-17 1956-10-02 Process for the production of plastic coatings or films
DEF22591A DE1148969B (en) 1956-04-05 1956-10-29 Procedure for flame retardant equipment
DEF21526A DE1025086B (en) 1956-04-05 1956-10-29 Lubricant additives
CH351825D CH351825A (en) 1956-04-05 1956-11-01 Method for sewing seam patterns with parallel beads on a zigzag sewing machine and presser foot for carrying out the method
FR1160553D FR1160553A (en) 1956-02-17 1956-11-20 Method for making parallel <<bugs>>, with zig-zag stitch sewing machines, and device for carrying out this method
US640035A US2977913A (en) 1956-02-17 1957-02-13 Method of sewing parallel rows of zigzag stitches
CH359134D CH359134A (en) 1956-04-05 1957-03-27 Process for the preparation of amidophosphoric acid derivatives
FR1177733D FR1177733A (en) 1956-04-05 1957-04-03 Amidophosphoric acid derivatives
GB11039/57A GB830800A (en) 1956-04-05 1957-04-04 Amidophosphoric acid derivatives
CH355316D CH355316A (en) 1956-04-05 1957-05-08 Registering speedometer for motor vehicles with a device for recording information other than the driving speed
FR1174947D FR1174947A (en) 1956-04-05 1957-05-10 Vehicle track recorder device
GB16236/57A GB813733A (en) 1956-04-05 1957-05-22 Device on recording motor vehicle speedometers

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
DE359134X 1956-04-05
DEF20264A DE1087109B (en) 1956-04-05 1956-04-05 Procedure for flame retardant equipment
DEF20584A DE1021526B (en) 1956-04-05 1956-05-11 Lubricant additives
DE355316X 1956-05-23
DEF22591A DE1148969B (en) 1956-04-05 1956-10-29 Procedure for flame retardant equipment
DE291056X 1956-10-29
DE120357X 1957-03-12

Publications (1)

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DE1148969B true DE1148969B (en) 1963-05-22

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Family Applications (4)

Application Number Title Priority Date Filing Date
DEF20264A Pending DE1087109B (en) 1948-11-13 1956-04-05 Procedure for flame retardant equipment
DEF20584A Pending DE1021526B (en) 1948-11-13 1956-05-11 Lubricant additives
DEF22591A Pending DE1148969B (en) 1948-11-13 1956-10-29 Procedure for flame retardant equipment
DEF21526A Pending DE1025086B (en) 1956-04-05 1956-10-29 Lubricant additives

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Application Number Title Priority Date Filing Date
DEF20264A Pending DE1087109B (en) 1948-11-13 1956-04-05 Procedure for flame retardant equipment
DEF20584A Pending DE1021526B (en) 1948-11-13 1956-05-11 Lubricant additives

Family Applications After (1)

Application Number Title Priority Date Filing Date
DEF21526A Pending DE1025086B (en) 1956-04-05 1956-10-29 Lubricant additives

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CH (5) CH120357A (en)
DE (4) DE1087109B (en)
FR (2) FR1177733A (en)
GB (2) GB830800A (en)

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US3311622A (en) * 1961-05-17 1967-03-28 Shulton Inc Substituted phosphonitrilic trimers
DE1163324B (en) * 1961-08-11 1964-02-20 Hoechst Ag Process for the production of pure phosphoric acid alkyl amide diamides
US3527564A (en) * 1968-04-15 1970-09-08 Stevens & Co Inc J P Process for carbonizing fibrous materials
US4530714A (en) * 1983-03-16 1985-07-23 Allied Corporation N-aliphatic and N,N-aliphatic phosphoric triamide urease inhibitors and urease inhibited urea based fertilizer compositions
US4539037A (en) * 1983-03-16 1985-09-03 Allied Corporation Urease inhibited urea based fertilizer compositions containing N-aryl-N-aliphatic phosphorotriamide compounds
US4540428A (en) * 1983-03-16 1985-09-10 Allied Corporation Phosphorotriamidate urease inhibitors and urease inhibited urea based fertilizer compositions
US4517002A (en) * 1983-03-16 1985-05-14 Allied Corporation Phosphorodiamide urease inhibitors and urease inhibited urea based fertilizer compositions
US4537614A (en) * 1983-03-16 1985-08-27 Allied Corporation S-aryl and S-aliphatic diamidophosphorothiolates as urease inhibitors and urease inhibited urea based fertilizer compositions
EP0119494A1 (en) * 1983-03-16 1984-09-26 Allied Corporation Urease inhibited urea based fertilizer compositions containing phosphorus compounds
US4518413A (en) * 1983-06-06 1985-05-21 Allied Corporation Poly-phosphorodiamide urease inhibitors and urease inhibited urea based fertilizer compositions
US4517003A (en) * 1983-06-08 1985-05-14 Allied Corporation N-acyl phosphoric triamide urease inhibitors and urease inhibited urea based fertilizer compositions
US4517007A (en) * 1983-06-09 1985-05-14 Allied Corporation Phosphoroamide urease inhibitors and urease inhibited urea based fertilizer compositions
GB2223054B (en) * 1988-09-21 1992-12-23 Yale Security Prod Ltd Cylinder locks
US5770771A (en) * 1997-01-21 1998-06-23 Albemarle Corporation Preparation of N-hydrocarbylthiophosphoric triamides
US5872293A (en) * 1997-01-21 1999-02-16 Albemarle Corporation Separating ammonium chloride from N-hydrocarbylphosphoric triamide or N-hydrocarbylthiophosphoric triamide
US5871667A (en) * 1997-01-21 1999-02-16 Albemarle Corporation Inhibiting ferrous metal corrosion by aqueous ammoniate solutions
US5955630A (en) * 1997-01-21 1999-09-21 Albemarle Corporation Recovery of N-hydrocarbylthiophosphoric triamides and N-hydrocarbylphosphoric triamides from reaction mixtures
US5883297A (en) * 1997-01-21 1999-03-16 Albemarle Corporation Preparation and recovery of N-hydrocarbylthiophosphoric triamides or N-hydrocarbylphosphoric triamides
GB2334294A (en) * 1998-02-14 1999-08-18 John Dennis Crummack Cylinder lock key engaging lock body
JP4121215B2 (en) 1999-05-17 2008-07-23 財団法人微生物化学研究会 Sulfostin analog, and method for producing sulfostine and its analog

Citations (1)

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DE831538C (en) * 1949-03-09 1952-02-14 Geigy Ag J R Process for impregnating cellulose material in order to reduce the flammability and / or to protect against attack by small organisms

Patent Citations (1)

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DE831538C (en) * 1949-03-09 1952-02-14 Geigy Ag J R Process for impregnating cellulose material in order to reduce the flammability and / or to protect against attack by small organisms

Also Published As

Publication number Publication date
CH351825A (en) 1961-01-31
CH120357A (en) 1927-06-01
GB830800A (en) 1960-03-23
DE1021526B (en) 1957-12-27
DE1025086B (en) 1958-02-27
FR1174947A (en) 1959-03-18
CH359134A (en) 1961-12-31
DE1087109B (en) 1960-08-18
GB813733A (en) 1959-05-21
CH291056A (en) 1953-05-31
CH355316A (en) 1961-06-30
FR1177733A (en) 1959-04-29

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