CS232346B1 - Processing of 3,9-(7,15-diazadispiro(5,1,5,3)hexadecan-15-yl)-2,4,8,1%-tetraoxa-3,9-diphosphaspiro(5,5)undecan - Google Patents
Processing of 3,9-(7,15-diazadispiro(5,1,5,3)hexadecan-15-yl)-2,4,8,1%-tetraoxa-3,9-diphosphaspiro(5,5)undecan Download PDFInfo
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- CS232346B1 CS232346B1 CS834698A CS469883A CS232346B1 CS 232346 B1 CS232346 B1 CS 232346B1 CS 834698 A CS834698 A CS 834698A CS 469883 A CS469883 A CS 469883A CS 232346 B1 CS232346 B1 CS 232346B1
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- Czechoslovakia
- Prior art keywords
- diphosphaspiro
- tetraoxa
- diazadispiro
- hexadecan
- formula
- Prior art date
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 title claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- -1 hexadecan-15-yl Chemical group 0.000 claims description 2
- OLZALNPHLPDXMK-UHFFFAOYSA-N dispiro[5.1.5^{8}.3^{6}]hexadecane Chemical compound C1CCCCC21CC1(CCCCC1)CCC2 OLZALNPHLPDXMK-UHFFFAOYSA-N 0.000 claims 1
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZOSPIRSWAQIPSU-UHFFFAOYSA-N 7,15-diazadispiro[5.1.5^{8}.3^{6}]hexadecane Chemical compound C1CCCCC21NC1(CCCCC1)CNC2 ZOSPIRSWAQIPSU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000002301 combined effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
Description
Vynélez sa týká 3,9-(7,15-diazadispiro[5,1,5, jjhexedekán-l5-yl)-2,4,8,10-tetreoxa-3,9-difosfaspiro[5,5]undekánu a spfisobu jeho přípravy.The invention relates to 3,9- (7,15-diazadispiro [5,1,5,6-hexedecan-15-yl) -2,4,8,10-tetreoxa-3,9-diphosphaspiro [5,5] undecane and spfisob. his preparation.
Stéricky bráněné aminy sú vysokoúčinné světelné stabilizátory polymérov. Fosfity patria v súčasnosti medzi významné druhy antioxidantov. Stéricky bráněné aminy inhibujú radikálové procesy, ktoré prebiehajú pri fotooxidácii polymérov a fosfity pSsobia pri termooxidáeii polymérov ako rozkladače peroxidov. Nevýhodou nízkomolekulových zlúčenín stéricky bráněných piperidínov je ich značná prchavosť a vypieratel’nosť.Sterically hindered amines are high-efficiency light stabilizers of polymers. Phosphites are currently among the important types of antioxidants. The sterically hindered amines inhibit the radical processes that take place in the photooxidation of polymers and phosphites act as peroxide decomposers in the thermooxidation of polymers. The disadvantage of low molecular weight sterically hindered piperidine compounds is their high volatility and washability.
Uvedené nevýhody tento vynález odstraňuje. Podstatou vynálezu je 3,9(7,15-diazadispiro [5,1,5,3] hexadekán-15-yl)-? ,4,8,10-3,9~tetraoxa-3,9-difosfaspiro[5,5]undekán vzorca 1These disadvantages are overcome by the present invention. The present invention provides 3,9 (7,15-diazadispiro [5,1,5,3] hexadecan-15-yl) -? 4,8,10-3,9-tetraoxa-3,9-diphosphaspiro [5,5] undecane of formula 1
ΠΠ
HNHN
P—NP-N
NH /1/NH / 1 /
Podstatou vynálezu je áalej spfisob přípravy zlúčeniny vzorca I, ktorý sa vyznačuje tým, že sa na 7,15-diazadispiro[5,1 ,5,3]hexadekán vzorca IIThe present invention further provides a process for the preparation of a compound of formula (I) which is characterized in that 7,15-diazadispiro [5,1,5,3] hexadecane of formula (II)
H /11/ pfisobí 3,9-dichlór-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5]undekénom vzorca IIIH (11) adds 3,9-dichloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro [5,5] undecene III
Λγ-Ο\ Cl~p\ Λ /P_CI /IIIZ o—' '—o v pomere 2:1 v suchom dimetylformamide, alebo v suchom benzéne alebo toluéne v přítomnosti trietylamínu. Λγ- Ο \ Cl p \ Λ / P_CI / IIIZ o "'s of 2: 1 in dry dimethylformamide, or in dry benzene or toluene in the presence of triethylamine.
Výhodou uvedeného vynálezu je jednak zvačéenie molekulovej hmotnosti stabilizátore a jednak příprava stabilizátore polymérov s kombinovaným účinkom, ktorý spája výhodné vlastnosti světelných stabilizátorov typu stéricky bráněných amínov a fosfitových antioxidantov.The advantage of the present invention is, on the one hand, to increase the molecular weight of the stabilizer and, on the other hand, to provide a stabilizer of combined effect polymers which combines the advantageous properties of light stabilizers of the hindered amine type and phosphite antioxidants.
Příklad 1Example 1
K roztoku 2,22 g (0,01 mol) 7,15-diazadispiro[5,1,5,3] hexadekánu v 20 ml suchého dimetylformamidu sa pri teplote okolo 20 °G za stálého miešania pomaly prikvapkáva roztok 1,265 g (0,005 mol) 3,9-dlčhlór-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5] undekénu v 15 ml suchého dimetylformamidu. Zmes sa ňalej mieša 5 h, potom sa vleje do 60 ml vody a silné zalkalizuje 4056 roztoku hydroxidu sodného. Vyextrahuje sa třikrát, chloroformem spojené extrakty sa vysušia bezvodým síranom sodným e^ozpúšťadlo sa odpaří. Zostávajúci tuhý podiel sa prekryštalizuje z etanolu. Získá sa produkt v podobě bielej kryStalickej látky s teplotou topenia v rozmedzí 129 až 132 °C.To a solution of 2,22 g (0,01 mol) of 7,15-diazadispiro [5,1,5,3] hexadecane in 20 ml of dry dimethylformamide, a solution of 1.265 g (0.005 mol) is slowly added dropwise with stirring at about 20 ° C. 3,9-Dichloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecene in 15 mL of dry dimethylformamide. The mixture was further stirred for 5 h, then poured into 60 ml of water and basified strongly with 4056 sodium hydroxide solution. It is extracted three times, the chloroform-combined extracts are dried over anhydrous sodium sulphate and the solvent is evaporated. The remaining solid was recrystallized from ethanol. The product is obtained in the form of a white crystalline substance, m.p. 129-132 ° C.
Elementárně analýza pře C33H58N4°4P2Elemental analysis for C 33 H 58 N 4 ° 4 P 2
Vypočítané: C = 62,24 56 H = 9,18 56 N = 8,80 56Calculated: C = 62.24 56 H = 9.18 56 N = 8.80 56
Nájdené: C = 62,32 56 H = 9,10 56 N = 8,72 %Found: C = 62.32 56 H = 9.10 56 N = 8.72%
Příklad 2Example 2
K roztoku 2,22 g (0,01 mol) 7,15-diazadispiro[5,1,5,3]hexadekánu a 1,4 ml trietylamínu v 50 ml suchého benzénu sa pri teplote okolo 20 °C za stálého miešania poaaly prikvapkáva roztok f,265 g (0,005 mol) 3,9-dichlór-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5jundekénu v 10 ml suchého benzénu. Reakčná zmes sa nechá pri tej istej teplote áalej miešať po dobu 24 h. Vzniknutý tuhý podiel sa odsaje, rozpustí v nasýtenom roztoku uhličitanu draselného a roztok sa dflkladne vyextrahuje éterom. Benzénový filtrát a éterické extrakty sa spoja, vysušia bezvodým síranom sodným a rozpúšťadlá sa odparia. Zostávajúci tuhý podiel sa prekryštalizuje z etanolu. Získá sa produkt v podobě bielej kryštalickej látky s teplotou topenia v rozmedzí 129 až 132 °C.To a solution of 2.22 g (0.01 mol) of 7,15-diazadispiro [5,1,5,3] hexadecane and 1.4 ml of triethylamine in 50 ml of dry benzene is slowly added dropwise at about 20 ° C with stirring. solution f, 265 g (0.005 mol) of 3,9-dichloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5 ]undecene in 10 ml of dry benzene. The reaction mixture was allowed to stir at the same temperature for 24 h. The resulting solid was filtered off with suction, dissolved in saturated potassium carbonate solution and extracted thoroughly with ether. The benzene filtrate and ethereal extracts were combined, dried over anhydrous sodium sulfate, and the solvents were evaporated. The remaining solid was recrystallized from ethanol. The product is obtained in the form of a white crystalline solid, m.p. 129-132 ° C.
Elementáma analýza pre C^^H^gN^O^PpElemental analysis for C ^^H H ^NNO ^P P
Vypočítané: Nájdené:Calculated: Found:
C = 62,24 % C = 62,10 %C = 62.24% C = 62.10%
H = 9,18 % H = 9,25 %H = 9.18% H = 9.25%
N = 8,80 % N = 8,65 %N = 8.80% N = 8.65%
IC spektrum (chloroform) v (N-H)=3 240, vas (C-H)=2 920,vs (C-H)=2 760, S (N-H) = 1 670, <5(C-H) = 1 450, e(P-O) = 1 180, 990 v (P-N)=850 cm’IC spectrum (chloroform) v (NH) = 3,240, v s (CH) = 2920, v s (CH) = 2760, S (NH) = 1670, <5 (CH) = 1450, e ( PO) = 1,180, 990 in (PN) = 850 cm -1
Vynález mé použitie v chémii polymérov pre přípravu stabilizátore s kombinovaným účinkom.The invention is my use in the chemistry of polymers for the preparation of stabilizers with combined effect.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS834698A CS232346B1 (en) | 1983-06-24 | 1983-06-24 | Processing of 3,9-(7,15-diazadispiro(5,1,5,3)hexadecan-15-yl)-2,4,8,1%-tetraoxa-3,9-diphosphaspiro(5,5)undecan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS834698A CS232346B1 (en) | 1983-06-24 | 1983-06-24 | Processing of 3,9-(7,15-diazadispiro(5,1,5,3)hexadecan-15-yl)-2,4,8,1%-tetraoxa-3,9-diphosphaspiro(5,5)undecan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS469883A1 CS469883A1 (en) | 1984-06-18 |
| CS232346B1 true CS232346B1 (en) | 1985-01-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS834698A CS232346B1 (en) | 1983-06-24 | 1983-06-24 | Processing of 3,9-(7,15-diazadispiro(5,1,5,3)hexadecan-15-yl)-2,4,8,1%-tetraoxa-3,9-diphosphaspiro(5,5)undecan |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS232346B1 (en) |
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1983
- 1983-06-24 CS CS834698A patent/CS232346B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS469883A1 (en) | 1984-06-18 |
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