DE953078C - Process for stabilizing triaethyleneiminophosphine oxide - Google Patents
Process for stabilizing triaethyleneiminophosphine oxideInfo
- Publication number
- DE953078C DE953078C DEF15454A DEF0015454A DE953078C DE 953078 C DE953078 C DE 953078C DE F15454 A DEF15454 A DE F15454A DE F0015454 A DEF0015454 A DE F0015454A DE 953078 C DE953078 C DE 953078C
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- stabilizing
- triaethyleneiminophosphine
- peroxides
- solutions
- 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
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- LHRMHPNVMOPZSG-UHFFFAOYSA-N N=P=O.C=C.C=C.C=C Chemical compound N=P=O.C=C.C=C.C=C LHRMHPNVMOPZSG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- MHFQUIMYQRETGU-UHFFFAOYSA-N C(C1)N1P(N1CC1)(N1CC1)OP(N1CC1)(N1CC1)N1CC1 Chemical compound C(C1)N1P(N1CC1)(N1CC1)OP(N1CC1)(N1CC1)N1CC1 MHFQUIMYQRETGU-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 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
- C07F9/547—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
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)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
Verfahren zum Stabilisieren von Triäthyleniminophosphinoxyd Es ist bekannt, daß Triäthyleniminophosphinoxyd die Eigenschaft besitzt, bei längerem Lagern, besonders bei erhöhter Temperatur und bei Anwesenheit von Luftfeuchtigkeit und Kohlensäure, von dem leichtlöslichen monomeren Zustand allmählich in polymere Formen überzugehen. Im Endzustand der Polymerisation liegt -die -Verbindung a=ls sehwierlöshiche hodhvi-skose und zähe Masse vor. Nicht nur die reine Verbindung polymerisiert, sondern auch die Lösungen der Verbindung. Da sich mit dem Fortschreiten des Polymerisationsprozesses Schwierigkeiten bei der Anwendung der Produkte ergeben, besteht das Bedürfnis, durch geeignete Zustände die Polymerisationsneigung des Triätrhylerniminopllhosphi-noxyds bzw. #gainer Lösungen wähnend der Lagerhail:tung mu verringern bzw. ganz zu.unterdrücken.Method of Stabilizing Triethyleniminophosphine Oxide It is known that triethyleniminophosphine oxide has the property, if stored for a long time, especially at high temperatures and in the presence of humidity and carbon dioxide, to gradually change from the easily soluble monomeric state to polymeric forms. In the final state of the polymerization, the compound a = ls visually soluble hodhvi-skose and tough mass before. Not only does the pure compound polymerize, but also the Solutions of the connection. As the polymerization process progresses If difficulties arise in the application of the products, there is a need to go through suitable states the tendency of the triethylamine iminoplphosphine oxide to polymerize or #gainer solutions during storage: tung must reduce or completely suppress.
Es wurde nun gefunden, daß man Triäthyleniminophosphinoxyd bzw. seine Lösungen dadurch stabilisieren kann, daß man der reinen Verbindung oder ihren Lösungen in organischen Lösungsmitteln wasserentziehende Stoffe oder Peroxyde zusetzt. Sowohl die wasserentziehenden Stoffe als auch die Peroxyde verzögern schon in geringer Konzentration das Nachdicken des Triäthyleniminophosphinoxyds. Als wasserentziehende Stoffe seien beispielsweise genannt: Phosphorpentoxyd, wasserfreies Natriumsulfat, wasserfreies Natriumcarbonat, gebrännter Kalk, Magnesiumperchlorat und Calciumchlorid. Als Peroxyde kommen vorzugsweise organische Peroxyde, die in den als Verdünnungsmittel für Triäthyleniminophosphinoxyd üblicherweise verwendeten aromatischen Lösungsmitteln, wie Benzol, Toluol, löslich sind, in Betracht, da sich mit denselben eine homogene Mischung bildet. Als besonders wirksame Stabilisierungsmittel seien beispielsweise genannt: Lauroylperoxyd, p-Chlorben:zoylperoxyd, Gu@molhydroperoxyd, tertiäres Butylhydroperoxyd.It has now been found that you can use Triethyleniminophosphinoxyd or his Solutions can be stabilized by using the pure compound or its solutions Adds dehydrating substances or peroxides in organic solvents. As well as the dehydrating substances as well as the peroxides retard a little Concentration thickening of the triethylene iminophosphine oxide. As dehydrating Examples of substances are: phosphorus pentoxide, anhydrous sodium sulfate, anhydrous sodium carbonate, calcined Lime, magnesium perchlorate and calcium chloride. The preferred peroxides are organic peroxides, which are used in commonly used as a diluent for Triethyleniminophosphinoxyd aromatic solvents, such as benzene, toluene, are soluble, as are forms a homogeneous mixture with them. As a particularly effective stabilizing agent may be mentioned, for example: lauroyl peroxide, p-chlorobenzene: zoyl peroxide, Gu @ molhydroperoxide, tertiary butyl hydroperoxide.
Die von den genannten Stoffen als Zusatz in Frage kommenden Mengen liegen üblicherweise zwischen ;etwa o,2 und etwa 50/0. Im allgemeinen genügen Mengen von etwa o;5 bis 2%. Dies hindert jedoch `nicht, daß in einzelnen Fällen auch größere als die angegebenen -Mengen verwendet werden.The quantities of the substances mentioned that can be used as additives are usually between; about 0.2 and about 50/0. In general, quantities are sufficient from about 0.5 to 2%. However, this does not prevent that in individual cases larger used as the specified amounts.
Es ist außerordentlich überraschend, daß durch den Zusatz der genannten Stoffe ein Stabilisierungseffekt erreicht wird, insbesondere, daß dieser Stabilisierungseffekt mit Peroxyden erzielt werden kann, da Peroxyde bekanntlich bei Verbindungen, die ein stickstoffhaltiges dreigliederiges Ringsystem enthalten, Polymerisationsvorgänge auslösen.It is extremely surprising that with the addition of the above Substances a stabilizing effect is achieved, in particular that this stabilizing effect can be achieved with peroxides, since peroxides are known to be used in compounds that contain a nitrogen-containing three-membered ring system, polymerisation processes trigger.
Auch bei bereits anpolymerisierten Produkten zeigen die genannten Verbindungen noch ihre polymerisationsverzögernde Wirkung.These also show in the case of products that have already been polymerized on Compounds still have their polymerisation-retarding effect.
Beispiel i ioo Gewichtsteile einer 8c%igen Lösung von Triäthyleniminophosphinoxyd in Benzol werden mit i Gewrichtste1l- Phöspihorpentoxyd vermischt. Erwärmt man die Mischung 3o Tage auf 55°, so erhält man eine immer noch. gut gießbare Masse, während eine ohne den Zusatz des Stabilisierungsmittels in gleicher Weise behandelte Probe zu einer festen und zähen Masse erstarrt ist.Example 100 parts by weight of an 8% solution of triethylene iminophosphine oxide in benzene are mixed with 1 weight of phosphorus pentoxide. If you warm them up Mix at 55 ° for 30 days, so you still get one. well pourable mass while a sample treated in the same way without the addition of the stabilizing agent has solidified into a solid and viscous mass.
Beispiel e ioo Gewichtsteile einer 80%igen Lösung von Triäthyleniminophosphinoxyd in Benzol werden mit i Gewichtsteil Lauroylperoxyd vermischt. Das Gemisch wird 2o Tage auf 6o° erwärmt. Nach dem Abkühlen liegt eine gut gießbare ölige Flüssigkeit vor, während eine ohne Stabilisatorzusatz 'unter glicichen Bedingungen ,erhitzte Probe von Triäthyleniminophosphinooxyd au einer festen und zähen Masse erstarrt tist.Example e 100 parts by weight of an 80% solution of Triethyleniminophosphinoxyd in benzene are mixed with 1 part by weight of lauroyl peroxide. The mixture is 2o Warmed to 60 ° for days. After cooling, there is an easily pourable oily liquid before, while one without added stabilizer 'under the same conditions, heated Sample of Triethyleniminophosphinooxyd solidified on a solid and viscous mass tist.
Beispiel 3 ioo Gewichtsteile einer schwachpolymerisierten. 9o%igen * Lösung von Triäthyleniminophosphinoxyd in Toluol, die eine sirupartige Konsistenz besitzt, werden mit 2 Gewichtsteilen Cumolhydroperoxyd vermischt und io Tage auf 50°. erwärmt. Nach dem Abkühlen erhält man eine weiche Paste, während eine entsprechende Probe von polymerisiertem Triäthyleniminophosphinoxyd, die in gleicher Weise ohne Zusatz von Peroxyd behandelt -wurde, zu einer härten Masse erstarrt.Example 3 100 parts by weight of a weakly polymerized. 9o% * Solution of triethyleniminophosphine oxide in toluene, which has a syrupy consistency owns, are mixed with 2 parts by weight of cumene hydroperoxide and 10 days on 50 °. warmed up. After cooling, a soft paste is obtained, while a corresponding one Sample of polymerized Triäthyleniminophosphinoxyd, which in the same way without Addition of peroxide was treated, solidified to a hard mass.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF15454A DE953078C (en) | 1954-08-13 | 1954-08-13 | Process for stabilizing triaethyleneiminophosphine oxide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF15454A DE953078C (en) | 1954-08-13 | 1954-08-13 | Process for stabilizing triaethyleneiminophosphine oxide |
Publications (1)
Publication Number | Publication Date |
---|---|
DE953078C true DE953078C (en) | 1956-11-29 |
Family
ID=7087900
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF15454A Expired DE953078C (en) | 1954-08-13 | 1954-08-13 | Process for stabilizing triaethyleneiminophosphine oxide |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE953078C (en) |
-
1954
- 1954-08-13 DE DEF15454A patent/DE953078C/en not_active Expired
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