GB1525262A - Zwitterionic compounds of phosphinic acids - Google Patents
Zwitterionic compounds of phosphinic acidsInfo
- Publication number
- GB1525262A GB1525262A GB34977/75A GB3497775A GB1525262A GB 1525262 A GB1525262 A GB 1525262A GB 34977/75 A GB34977/75 A GB 34977/75A GB 3497775 A GB3497775 A GB 3497775A GB 1525262 A GB1525262 A GB 1525262A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- compound
- formula
- hydrocarbon radical
- zwitterionic
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 11
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title abstract 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 abstract 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000002216 antistatic agent Substances 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 238000005188 flotation Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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)
Abstract
1525262 Zwitterionic salts of phosphinic acids HOECHST AG 22 Aug 1975 [22 Aug 1974] 34977/75 Heading C2P The invention comprises (a) zwitterionic compounds having the general Formula (I):- wherein R is a non-aromatic hydrocarbon radical, R 1 , R 2 and R 3 , any two or more of which may be the same or different, each represents a hydrogen atom or a non-aromatic hydrocarbon radical and B 4 is a non-aromatic hydrocarbon radical which is unsubstituted or substituted by one or more aryl groups, and (b) zwitterionic compounds having the general formula:- wherein R, R 1 , R 2 , R 3 , any two or more of which may be the same or different, are as defined above, and R 5 is a non-aromatic bivalent hydrocarbon radical which is unsubstituted or substituted by one or more aryl groups and/or interrupted by one or more arylene groups. The compounds I and II may be obtained by reacting a compound:- with a compound of the formula B 3 R 4 NH or a compound of the formula R 3 NHR 5 NHR 3 respectively. The invention also includes salt derivatives of the defined compounds, e.g. the hydrochlorides. Examples are given for the production of compounds I in which R is CH 3 , R 1 , R 2 and R 3 are each H and R 4 is cyclohexyl and of compounds II in which R is CH 3 , R 1 , R 2 and R 3 are each H and R 5 is derived from bis-(4-amino-cyclohexyl)-methane, 1,3-diaminopropane and hexamethylenediamine respectively. An example is also given in which the hydrochloride salt (V) of the formula:- is obtained by reacting the 1,3 diamino propane derivative (IV) of the formula:- with ethanolic hydrochloric acid, the compound V being reconverted to compound IV by treatment with alcoholic KOH. The products I and II are useful as anti-static agents, primers for metallic surfaces, as disinfectants, and as flotation and emulsifying auxiliaries.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2440239A DE2440239A1 (en) | 1974-08-22 | 1974-08-22 | INNER AMMONIUM SALTS OF PHOSPHIC ACIDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1525262A true GB1525262A (en) | 1978-09-20 |
Family
ID=5923804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34977/75A Expired GB1525262A (en) | 1974-08-22 | 1975-08-22 | Zwitterionic compounds of phosphinic acids |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5143726A (en) |
| AT (1) | AT332884B (en) |
| BE (1) | BE832681A (en) |
| CA (1) | CA1051920A (en) |
| DE (1) | DE2440239A1 (en) |
| FR (1) | FR2282431A1 (en) |
| GB (1) | GB1525262A (en) |
| IT (1) | IT1041954B (en) |
| NL (1) | NL7509753A (en) |
| ZA (1) | ZA755366B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5190934A (en) * | 1989-06-03 | 1993-03-02 | Ciba-Geigy Corporation | P-subsituted propane-phosphinic acid compounds |
| US5190933A (en) * | 1987-12-04 | 1993-03-02 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| US5229379A (en) * | 1990-06-22 | 1993-07-20 | Ciba-Geigy Corporation | Certain n-substituted-amino-alkane phosphinic acid derivatives having anti-epileptic properties |
| US5243062A (en) * | 1984-10-12 | 1993-09-07 | Ciba-Geigy Corporation | Substituted propane-phosphonous acid compounds |
| US5300679A (en) * | 1987-12-04 | 1994-04-05 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| US5332729A (en) * | 1992-05-08 | 1994-07-26 | Ciba-Geigy Corporation | N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
| US5376684A (en) * | 1991-11-21 | 1994-12-27 | Ciba-Geigy Corporation | Aminoalkanephosphinic acids and salts thereof |
| US5457095A (en) * | 1984-10-12 | 1995-10-10 | Ciba-Geigy Corporation | Substituted propane-phosponous acid compounds |
| US5461040A (en) * | 1989-05-13 | 1995-10-24 | Ciba-Geigy Corporation | Substituted aminoalkylphosphinic acids |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2723137C3 (en) * | 1977-05-23 | 1980-06-26 | Hoechst Ag, 6000 Frankfurt | Process for the preparation of methyl [2- <2,4,6tribromophenylcarbamoyl-) ethyl] phosphinic acid |
| GB8728483D0 (en) * | 1987-12-04 | 1988-01-13 | Ciba Geigy Ag | Chemical compounds |
| CN103127876B (en) * | 2011-11-22 | 2015-01-07 | 中国科学院大连化学物理研究所 | Quaternary amination organic phosphine surfactant and synthetic method thereof |
-
1974
- 1974-08-22 DE DE2440239A patent/DE2440239A1/en not_active Withdrawn
-
1975
- 1975-08-15 NL NL7509753A patent/NL7509753A/en not_active Application Discontinuation
- 1975-08-20 IT IT26470/75A patent/IT1041954B/en active
- 1975-08-20 JP JP50100238A patent/JPS5143726A/ja active Pending
- 1975-08-21 CA CA234,011A patent/CA1051920A/en not_active Expired
- 1975-08-21 ZA ZA00755366A patent/ZA755366B/en unknown
- 1975-08-21 AT AT649675A patent/AT332884B/en not_active IP Right Cessation
- 1975-08-21 FR FR7525875A patent/FR2282431A1/en active Granted
- 1975-08-22 BE BE159411A patent/BE832681A/en unknown
- 1975-08-22 GB GB34977/75A patent/GB1525262A/en not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5457095A (en) * | 1984-10-12 | 1995-10-10 | Ciba-Geigy Corporation | Substituted propane-phosponous acid compounds |
| US5243062A (en) * | 1984-10-12 | 1993-09-07 | Ciba-Geigy Corporation | Substituted propane-phosphonous acid compounds |
| US5190933A (en) * | 1987-12-04 | 1993-03-02 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| US5300679A (en) * | 1987-12-04 | 1994-04-05 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| US5461040A (en) * | 1989-05-13 | 1995-10-24 | Ciba-Geigy Corporation | Substituted aminoalkylphosphinic acids |
| US5190934A (en) * | 1989-06-03 | 1993-03-02 | Ciba-Geigy Corporation | P-subsituted propane-phosphinic acid compounds |
| US5229379A (en) * | 1990-06-22 | 1993-07-20 | Ciba-Geigy Corporation | Certain n-substituted-amino-alkane phosphinic acid derivatives having anti-epileptic properties |
| US5545631A (en) * | 1990-06-22 | 1996-08-13 | Ciba-Geigy Corporation | N-substituted aminoalkanephosphinic acid derivatives, compositions thereof, and their use as anti-epileptics |
| US5376684A (en) * | 1991-11-21 | 1994-12-27 | Ciba-Geigy Corporation | Aminoalkanephosphinic acids and salts thereof |
| US5500418A (en) * | 1991-11-21 | 1996-03-19 | Ciba-Geigy Corporation | Aminoalkanephosphinic acids and salts thereof |
| US5332729A (en) * | 1992-05-08 | 1994-07-26 | Ciba-Geigy Corporation | N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
| US5424441A (en) * | 1992-05-08 | 1995-06-13 | Ciba-Geigy Corporation | N-aralkyl-and N-heteroaralkyl-aminoalkanephosphinic acids |
| AU662404B2 (en) * | 1992-05-08 | 1995-08-31 | Novartis Ag | Novel N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2440239A1 (en) | 1976-03-04 |
| IT1041954B (en) | 1980-01-10 |
| FR2282431B1 (en) | 1978-12-08 |
| AT332884B (en) | 1976-10-25 |
| CA1051920A (en) | 1979-04-03 |
| BE832681A (en) | 1976-02-23 |
| ATA649675A (en) | 1976-02-15 |
| JPS5143726A (en) | 1976-04-14 |
| ZA755366B (en) | 1976-08-25 |
| FR2282431A1 (en) | 1976-03-19 |
| NL7509753A (en) | 1976-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |