GB1467304A - Substituted aminoalkanephosphonic acid esters - Google Patents
Substituted aminoalkanephosphonic acid estersInfo
- Publication number
- GB1467304A GB1467304A GB3274574A GB3274574A GB1467304A GB 1467304 A GB1467304 A GB 1467304A GB 3274574 A GB3274574 A GB 3274574A GB 3274574 A GB3274574 A GB 3274574A GB 1467304 A GB1467304 A GB 1467304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- prepared
- optionally substituted
- alkyl groups
- 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
- 239000002253 acid Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000003063 flame retardant Substances 0.000 abstract 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1467304 Substituted alkanephosphonates CIBA-GEIGY AG 24 July 1974 [26 July 1973] 32745/74 Heading C2P [Also in Division C3] The invention comprises compounds of Formula I and of Formula II where R<SP>1</SP> and R<SP>3</SP> are identical C 2-10 alkyl groups or together denote -(CH 2 ) 3 - which is optionally substituted by 1 or 2 C 1-3 alkyl groups; a is 0, 1 or 2; b is 0 or 1; R<SP>5</SP> is H or CH 3 ; R<SP>4</SP> is H, C 1-4 alkyl, optionally substituted aryl, or furyl; R<SP>5</SP> is H or C 1-4 alkyl, or R<SP>4</SP> and R<SP>5</SP> together denote -(CH 2 ) 3 - which is optionally substituted by 1 or 2 C 1-3 alkyl groups; and R<SP>6</SP> is H or CH 3 . The compounds of Formula I may be prepared by hydrogenating corresponding compounds of Formula II catalytically at 20‹ to 150‹ C. Picrates of the compounds of Formula I are prepared. The compounds of Formula II may be prepared by reacting corresponding compounds of Formula III with acrylonitrile at 30‹ to 150‹ C. and at a mole ratio of between 1 : 1 to 1 : 1À5. The intermediates of Formula III may be prepared by subjecting corresponding compounds of Formula V to gentle aminating hydrogenation or, where R<SP>5</SP> is H, by catalytically hydrogenating corressponding compounds of Formula IV at 20‹ to 150‹ C. Picrates of the compounds of Formula III are prepared. The compounds of Formula I may be used as flame-retardant curing agents or as flameretardant additives for epoxy resins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1092273A CH584232A5 (en) | 1973-07-26 | 1973-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1467304A true GB1467304A (en) | 1977-03-16 |
Family
ID=4368235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3274574A Expired GB1467304A (en) | 1973-07-26 | 1974-07-24 | Substituted aminoalkanephosphonic acid esters |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5041818A (en) |
| CH (1) | CH584232A5 (en) |
| DE (1) | DE2435438A1 (en) |
| FR (2) | FR2245666B1 (en) |
| GB (1) | GB1467304A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985000038A1 (en) * | 1983-06-17 | 1985-01-03 | Kenogard Ab | Guanidated aminophosphonic acid compounds |
| WO2005048715A2 (en) * | 2003-11-24 | 2005-06-02 | Bioagency Ag | Organophosphoric compounds and use thereof |
| WO2010108063A1 (en) * | 2009-03-19 | 2010-09-23 | Wyeth Llc | Methods for the preparation of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]phosphonic acid and precursors thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH22224A (en) * | 1983-01-28 | 1988-07-01 | Schering Corp | Phosphorus containing amide compounds and pharmaceutical compositions containing them |
-
1973
- 1973-07-26 CH CH1092273A patent/CH584232A5/xx not_active IP Right Cessation
-
1974
- 1974-07-23 DE DE19742435438 patent/DE2435438A1/en not_active Withdrawn
- 1974-07-24 GB GB3274574A patent/GB1467304A/en not_active Expired
- 1974-07-25 FR FR7425871A patent/FR2245666B1/fr not_active Expired
- 1974-07-26 JP JP8597074A patent/JPS5041818A/ja active Pending
- 1974-10-25 FR FR7435828A patent/FR2240925B1/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985000038A1 (en) * | 1983-06-17 | 1985-01-03 | Kenogard Ab | Guanidated aminophosphonic acid compounds |
| WO2005048715A2 (en) * | 2003-11-24 | 2005-06-02 | Bioagency Ag | Organophosphoric compounds and use thereof |
| WO2005048715A3 (en) * | 2003-11-24 | 2005-07-28 | Bioagency Ag | Organophosphoric compounds and use thereof |
| WO2010108063A1 (en) * | 2009-03-19 | 2010-09-23 | Wyeth Llc | Methods for the preparation of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]phosphonic acid and precursors thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2240925A1 (en) | 1975-03-14 |
| JPS5041818A (en) | 1975-04-16 |
| FR2245666A1 (en) | 1975-04-25 |
| FR2240925B1 (en) | 1976-10-22 |
| DE2435438A1 (en) | 1975-02-06 |
| FR2245666B1 (en) | 1978-01-20 |
| CH584232A5 (en) | 1977-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |