GB830800A - Amidophosphoric acid derivatives - Google Patents
Amidophosphoric acid derivativesInfo
- Publication number
- GB830800A GB830800A GB11039/57A GB1103957A GB830800A GB 830800 A GB830800 A GB 830800A GB 11039/57 A GB11039/57 A GB 11039/57A GB 1103957 A GB1103957 A GB 1103957A GB 830800 A GB830800 A GB 830800A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- diamide
- mixed
- amidophosphoric
- polymers
- 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.)
- Expired
Links
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 title abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 12
- 239000002253 acid Substances 0.000 abstract 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 9
- 229920000642 polymer Polymers 0.000 abstract 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 8
- -1 cycloaliphatic Chemical group 0.000 abstract 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- 229910021529 ammonia Inorganic materials 0.000 abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 abstract 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- 229910018894 PSCl3 Inorganic materials 0.000 abstract 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 2
- IQLPGLICPZNTPK-UHFFFAOYSA-N [P].OS(Cl)(=O)=O Chemical compound [P].OS(Cl)(=O)=O IQLPGLICPZNTPK-UHFFFAOYSA-N 0.000 abstract 2
- 235000019270 ammonium chloride Nutrition 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- 238000004079 fireproofing Methods 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 239000003879 lubricant additive Substances 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- CIGVVIDJAGCNSW-UHFFFAOYSA-N n-diaminophosphinothioyl-n-propylpropan-1-amine Chemical compound CCCN(P(N)(N)=S)CCC CIGVVIDJAGCNSW-UHFFFAOYSA-N 0.000 abstract 2
- BWISTDKIQRHPRO-UHFFFAOYSA-N n-dichlorophosphinothioyl-n-propylpropan-1-amine Chemical compound CCCN(P(Cl)(Cl)=S)CCC BWISTDKIQRHPRO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 229920000570 polyether Polymers 0.000 abstract 2
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- XUOUPEUPYLYUPF-UHFFFAOYSA-N amino-(piperidin-1-ylamino)phosphinic acid Chemical compound N1(CCCCC1)NP(N)(O)=O XUOUPEUPYLYUPF-UHFFFAOYSA-N 0.000 abstract 1
- 230000003712 anti-aging effect Effects 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 239000010696 ester oil Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- AGXSEIPWEZUSLR-UHFFFAOYSA-N n-diaminophosphinothioyl-n-ethylethanamine Chemical compound CCN(CC)P(N)(N)=S AGXSEIPWEZUSLR-UHFFFAOYSA-N 0.000 abstract 1
- BXTWMYNXJKPDER-UHFFFAOYSA-N n-diaminophosphinothioyl-n-methyl-1-phenylmethanamine Chemical compound NP(=S)(N)N(C)CC1=CC=CC=C1 BXTWMYNXJKPDER-UHFFFAOYSA-N 0.000 abstract 1
- GUIDDMDCKCUKEZ-UHFFFAOYSA-N n-dichlorophosphinothioyl-n-ethylethanamine Chemical compound CCN(CC)P(Cl)(Cl)=S GUIDDMDCKCUKEZ-UHFFFAOYSA-N 0.000 abstract 1
- REJJEMHCFFQYTN-UHFFFAOYSA-N n-dichlorophosphinothioyl-n-methyl-1-phenylmethanamine Chemical compound ClP(=S)(Cl)N(C)CC1=CC=CC=C1 REJJEMHCFFQYTN-UHFFFAOYSA-N 0.000 abstract 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 238000009987 spinning Methods 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Computer Networks & Wireless Communication (AREA)
- Signal Processing (AREA)
- Fireproofing Substances (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lock And Its Accessories (AREA)
Abstract
Lubricating oil compositions comprise as high-pressure and anti-ageing additives amidophosphoric acid derivatives of the general formula <FORM:0830800/III/1> wherein X represents oxygen or sulphur, Y1 and Y2 represent a hydrocarbon radical which may be saturated or unsaturated, aliphatic, cycloaliphatic, aryl or aralkyl and may be substituted e.g. by halogen, or Y1 may be hydrogen or Y1 and Y2 together with the nitrogen atom form a heterocyclic radical, e.g. an ethyleneimine, pyrrolidine, piperidine, hexamethyleneimine or morpholine radical, and n denotes any integer. The lubricating oils may be mineral or synthetic in origin, suitable synthetic oils being polyether, polyester or poly-ether-ester oils. A specific polyether oil mentioned is one based on tetrahydrofurane and ethylene oxide.ALSO:The invention comprises amidophosphoric acid derivatives of the general formula <FORM:0830800/IV (b)/1> wherein X represents oxygen or sulphur, Y1 and Y2 represent a hydrocarbon radical which may be saturated or unsaturated, aliphatic, cycloaliphatic, aryl or aralkyl and may be substituted, e.g. by halogen, or Y1 may be hydrogen or Y1 and Y2 together with the nitrogen atom form a heterocyclic radical, e.g. an ethyleneimine, pyrrolidine, piperidine, hexamethyleneimine or morpholine radical, and n denotes any integer. They are prepared by reacting ammonia with an amidophosphoric acid halide of the general formula <FORM:0830800/IV (b)/2> wherein Z1 and Z2 represent the same or different halogen atoms at room temperature or with cooling, preferably in an inert solvent, e.g. carbon tetrachloride, benzene, chlorobenzene, ethyl acetate or ether. The products are used in fireproofing compositions and as lubricant additives. In examples there are prepared by the action of dry ammonia gas on the appropriate amidophosphoric acid halide in solution in benzene, carbon tetrachloride or methylene chloride: (1) a mixture of monomeric N-diethylamidophosphoric acid diamide and the polymers formed therefrom by the splitting out of ammonia from N-diethylamidophosphoric acid chloride; (2) monomeric N-di-n-butyl-amidophosphoric acid diamide mixed with polymers thereof from N-di-n-butylamido-phosphoric acid diamide mixed with polymers thereof from N - di - n - butylamido - phosphoric acid dichloride; (3) N-morpholidophosphoric acid diamide from N-morpholidophosphoric acid dichloride; (4) N-piperidyl-phosphoric acid diamide from N-piperyl-phosphoric acid dichloride; (5) N-b -chlorethylamido-phosphoric acid diamide mixed with ammonium chloride from N-b -chlorethylamidophosphoric acid dichloride; (6) N-dimethylamidophosphoric acid diamide mixed with NH4Cl from N-dimethylamidophosphoric acid dichloride; (7) diethylamidothiophosphoric acid diamide from diethylamidothiophosphoric acid dichloride; (8) dipropylamidothiophosphoric acid diamide mixed with polymers thereof from dipropylamidothiophosphoric acid dichloride; (9) tert.-octylamidothiophosphoric acid diamide mixed with polymers thereof from tert.-octylamidothiophosphoric acid dichloride, obtainable by reacting tert.-octylamine with phosphorus sulphochloride in methylene chloride; (10) morpholidothiophosphoric acid diamide from morpholidothiophosphoric acid dichloride obtainable from morpholine and PSCl3; (11) N-methylbenzylamidothiophosphoric acid diamide from N-methylbenzylamidothiophosphoric acid dichloride, obtainable from N-methylbenzylamide and PSCl3.ALSO:The invention comprises amidophosphoric acid derivatives of the general formula <FORM:0830800/IV (a)/1> wherein X represents oxygen or sulphur, Y1 and Y2 represent a hydrocarbon radical which may be saturated or unsaturated, aliphatic, cycloaliphatic, aryl or aralkyl and may be substituted, e.g. by halogen, or Y1 may be hydrogen or Y1 and Y2 together with the nitrogen atom form a heterocyclic radical, e.g. an ethyleneimine, pyrrolidine, piperidine, hexamethyleneimine or morpholine radical, and n denotes any integer. They are prepared by reacting ammonia with an amidophosphoric acid halide of the general formula <FORM:0830800/IV (a)/2> wherein Z1 and Z2 represent the same or different halogen atoms at room temperature or with cooling, preferably in an inert solvent, e.g. carbon tetrachloride, benzene, chlorobenzene, ethyl acetate or ether. The products may be incorporated in spinning and casting masses for the production of shaped articles and are used in fireproofing compositions and as lubricant additives. In examples there are prepared by the action of dry ammonia gas on the appropriate amidophosphoric acid halide in solution in benzene, carbon tetrachloride or methylene chloride; (1) a mixture of monomeric N-diethylamidophosphoric acid diamide and the polymers formed therefrom by the splitting out of ammonia from N-diethylamidophosphoric acid chloride; (2) monomeric N-di-n-butyl-amidophosphoric acid diamide mixed with polymers thereof from N-di-n-butylamido-phosphoric acid dichloride; (8) dipropylamidothiophosphoric acid diamide mixed with polymers thereof from dipropylamidothiophosphoric acid dichloride; (9) tert.-octylamidothiophosphoric acid diamide mixed with polymers thereof from tert.-octylamidothiophosphoric acid dichloride, obtainable by reacting tert.-octylamine with phosphorus sulphochloride in methylene chloride.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF20264A DE1087109B (en) | 1956-04-05 | 1956-04-05 | Procedure for flame retardant equipment |
DE359134X | 1956-04-05 | ||
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)
Publication Number | Publication Date |
---|---|
GB830800A true GB830800A (en) | 1960-03-23 |
Family
ID=27561247
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11039/57A Expired GB830800A (en) | 1956-04-05 | 1957-04-04 | Amidophosphoric acid derivatives |
GB16236/57A Expired GB813733A (en) | 1956-04-05 | 1957-05-22 | Device on recording motor vehicle speedometers |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16236/57A Expired GB813733A (en) | 1956-04-05 | 1957-05-22 | Device on recording motor vehicle speedometers |
Country Status (4)
Country | Link |
---|---|
CH (5) | CH120357A (en) |
DE (4) | DE1087109B (en) |
FR (2) | FR1177733A (en) |
GB (2) | GB830800A (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1163324B (en) * | 1961-08-11 | 1964-02-20 | Hoechst Ag | Process for the production of pure phosphoric acid alkyl amide diamides |
US3311622A (en) * | 1961-05-17 | 1967-03-28 | Shulton Inc | Substituted phosphonitrilic trimers |
EP0119494A1 (en) * | 1983-03-16 | 1984-09-26 | Allied Corporation | Urease inhibited urea based fertilizer compositions containing phosphorus compounds |
EP0119487A1 (en) * | 1983-03-16 | 1984-09-26 | Allied Corporation | Novel N-aliphatic and N,N-aliphatic phosphoric triamide urease inhibitors and urease inhibited urea based fertilizer compositions |
EP0119495A1 (en) * | 1983-03-16 | 1984-09-26 | Allied Corporation | S-aryl and S-aliphatic diamidophosphorothiolates as 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 |
US4517002A (en) * | 1983-03-16 | 1985-05-14 | Allied Corporation | Phosphorodiamide 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 |
US4518413A (en) * | 1983-06-06 | 1985-05-21 | Allied Corporation | Poly-phosphorodiamide 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 |
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 |
US5883297A (en) * | 1997-01-21 | 1999-03-16 | Albemarle Corporation | Preparation and recovery of N-hydrocarbylthiophosphoric triamides or N-hydrocarbylphosphoric triamides |
US5955630A (en) * | 1997-01-21 | 1999-09-21 | Albemarle Corporation | Recovery of N-hydrocarbylthiophosphoric triamides and N-hydrocarbylphosphoric triamides from reaction mixtures |
EP1184388A1 (en) * | 1999-05-17 | 2002-03-06 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Sulphostin analogues and processes for the preparation of sulphostin and analogues thereof |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3527564A (en) * | 1968-04-15 | 1970-09-08 | Stevens & Co Inc J P | Process for carbonizing fibrous materials |
GB2223054B (en) * | 1988-09-21 | 1992-12-23 | Yale Security Prod Ltd | Cylinder locks |
GB2334294A (en) * | 1998-02-14 | 1999-08-18 | John Dennis Crummack | Cylinder lock key engaging lock body |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
1926
- 1926-03-26 CH CH120357D patent/CH120357A/en unknown
-
1950
- 1950-12-22 CH CH291056D patent/CH291056A/en unknown
-
1956
- 1956-04-05 DE DEF20264A patent/DE1087109B/en active Pending
- 1956-05-11 DE DEF20584A patent/DE1021526B/en active Pending
- 1956-10-29 DE DEF22591A patent/DE1148969B/en active Pending
- 1956-10-29 DE DEF21526A patent/DE1025086B/en active Pending
- 1956-11-01 CH CH351825D patent/CH351825A/en unknown
-
1957
- 1957-03-27 CH CH359134D patent/CH359134A/en unknown
- 1957-04-03 FR FR1177733D patent/FR1177733A/en not_active Expired
- 1957-04-04 GB GB11039/57A patent/GB830800A/en not_active Expired
- 1957-05-08 CH CH355316D patent/CH355316A/en unknown
- 1957-05-10 FR FR1174947D patent/FR1174947A/en not_active Expired
- 1957-05-22 GB GB16236/57A patent/GB813733A/en not_active Expired
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US4539037A (en) * | 1983-03-16 | 1985-09-03 | Allied Corporation | Urease inhibited urea based fertilizer compositions containing N-aryl-N-aliphatic phosphorotriamide compounds |
EP0119494A1 (en) * | 1983-03-16 | 1984-09-26 | Allied Corporation | Urease inhibited urea based fertilizer compositions containing phosphorus compounds |
EP0119487A1 (en) * | 1983-03-16 | 1984-09-26 | Allied Corporation | Novel N-aliphatic and N,N-aliphatic phosphoric triamide urease inhibitors and urease inhibited urea based fertilizer compositions |
EP0119495A1 (en) * | 1983-03-16 | 1984-09-26 | Allied Corporation | S-aryl and S-aliphatic diamidophosphorothiolates as 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 |
US4540428A (en) * | 1983-03-16 | 1985-09-10 | Allied Corporation | Phosphorotriamidate urease inhibitors and urease inhibited urea based fertilizer compositions |
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 |
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 |
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 |
US5883297A (en) * | 1997-01-21 | 1999-03-16 | Albemarle Corporation | Preparation and recovery of N-hydrocarbylthiophosphoric triamides or N-hydrocarbylphosphoric triamides |
US5955630A (en) * | 1997-01-21 | 1999-09-21 | Albemarle Corporation | Recovery of N-hydrocarbylthiophosphoric triamides and N-hydrocarbylphosphoric triamides from reaction mixtures |
EP1184388A1 (en) * | 1999-05-17 | 2002-03-06 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Sulphostin analogues and processes for the preparation of sulphostin and analogues thereof |
EP1184388A4 (en) * | 1999-05-17 | 2002-10-16 | Zaidan Hojin Biseibutsu | Sulphostin analogues and processes for the preparation of sulphostin and analogues thereof |
US6579989B1 (en) | 1999-05-17 | 2003-06-17 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Sulphostin analogue and process for producing sulphostin and its analogue |
Also Published As
Publication number | Publication date |
---|---|
DE1087109B (en) | 1960-08-18 |
DE1148969B (en) | 1963-05-22 |
GB813733A (en) | 1959-05-21 |
CH351825A (en) | 1961-01-31 |
DE1021526B (en) | 1957-12-27 |
CH355316A (en) | 1961-06-30 |
CH359134A (en) | 1961-12-31 |
FR1174947A (en) | 1959-03-18 |
DE1025086B (en) | 1958-02-27 |
FR1177733A (en) | 1959-04-29 |
CH291056A (en) | 1953-05-31 |
CH120357A (en) | 1927-06-01 |
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