IL24318A - Metal diallyl phosphate resins and process for their preparation - Google Patents
Metal diallyl phosphate resins and process for their preparationInfo
- Publication number
- IL24318A IL24318A IL2431865A IL2431865A IL24318A IL 24318 A IL24318 A IL 24318A IL 2431865 A IL2431865 A IL 2431865A IL 2431865 A IL2431865 A IL 2431865A IL 24318 A IL24318 A IL 24318A
- Authority
- IL
- Israel
- Prior art keywords
- diallyl
- phosphate
- metal
- diallyl phosphate
- resins
- Prior art date
Links
- 229910019142 PO4 Inorganic materials 0.000 title claims description 23
- 239000010452 phosphate Substances 0.000 title claims description 19
- 239000011347 resin Substances 0.000 title claims description 17
- 229920005989 resin Polymers 0.000 title claims description 17
- 229910052751 metal Inorganic materials 0.000 title claims description 13
- 239000002184 metal Substances 0.000 title claims description 13
- -1 diallyl phosphate Chemical compound 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 235000021317 phosphate Nutrition 0.000 claims description 22
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 229920001523 phosphate polymer Polymers 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 2
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- JUWGUJSXVOBPHP-UHFFFAOYSA-B titanium(4+);tetraphosphate Chemical compound [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JUWGUJSXVOBPHP-UHFFFAOYSA-B 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Metal phosphate resins process for their preparation ISRAEL MINING INDUSTRIES FOR RESEARCH AND DEVELOPMENT This invention consists in insoluble synthetic resins being polymers or copolymers derived from metal diallyl phosphates of the formula where is a metal having a valency of from 1 to 4 and may also be and n is an integer of from 1 to Typical representatives of monovalent metals are the alkali metals divalent metals include a wide range of metals of different groups of the Periodic Table of alkaline earth metals such as transition such as and example of tervalent metals is aluminium and of valent metals is Metal diallyl phosphate resins according to the tion are valuable In addition they have been found to poesees a property which has been quite that they can absorb water selectively from organic wet gases and the and that they can readily be freed from the absorbed water with a small expenditure of energy by various different such as retransfer of the water to a solvent This property can be used either for the tion of the matter or for the recovery of pure water as described in an Israel Patent Specification They also exhibit selective absorption with respect to organic eolvents and may therefore be used for the separation of such solvents from each for poly diallyl can be used for the separation of mercaptanee from a Attempts made hitherto to prepare diallyl phosphate resins have Efforts to prepare resins with an approximately similar structure have been reported by Kennedy at This consisted in saponifying polytriallyl phosphate with aqueous alkali metal then acidulating the reaction mixture and neutralizing the resultant polyacid with inorganic salt of the desired though one of the allyloxy groups of the polytriallyl phosphate is more readily saponifiable than the remaining diallyl phosphates could not be produced in this The invention thus provides a process for the preparation of the new metal or ammonium polydiallyl phosphates and their which is a initiated merization or eopolymerisation of monomeric metal diallyl phosphate by itself or together with another monomer such as triallyl phosphate or Polymerization can be initiated by the irradiation of the reaction mixture with ultraviolet rays or any other conventional means for producing free The invention is illustrated by the following Examples to which it is not Example 1 10 g of sodium diallyl phosphate was refluxed with stirring in 20 ml of benzene containing g of benzoyl peroxide as an initiator at about under a nitrogen atmosphere for The mixture obtained was washed first with ethyl then with and whereby g of colourless insoluble polymeric sodium diallyl phosphate resin was It contained and organic such as ether and Its solubility in water was less than by In a aqueous no solubility could be Example 2 10 g of sodium diallyl phosphate was heated with stirring in 30 ml of xylene containing g of peroxide as an initiator under a slow stream of dry nitrogen at for 24 while being constantly exposed to The resultant mixture was further treated as in Example whereby 5 g of dry polymeric sodium diallyl phosphate resin was The properties of the resins were the same those of the resin obtained according to 3 Portions of the polymeric sodium diallyl phosphate obtained in accordance with Example 2 were mixed with aqueous solutions of aluminium or ferric After approximately minutes the mixtures were washed with water until and The solids obtained were analyzed and found to contain respectively aluminium and Example 4 A solution of 10 g of sodium diallyl phosphate in 5 ml of water containing ml of a aqueous solution of hydrogen peroxide was heated under nitrogen at for 30 hours while being irradiated by a source of After washing and 5 g of polymeric sodium diallyl phosphate resin was whose properties were the same as those of the resin obtained according to Example 1 ν Example 5 a solution of cobaltous diallyl phosphate in containing benzoyl peroxide in an amount of by weight of the monomer was refluxed for 12 hours in an inert The resultant benzene insoluble formed was washed and dried as described in Example This resin thus produced is blue when dry and turns upon contact with Similar colour changes were not observed upon contacting this resin with dry Example 6 A aqueous solution of diallyl was with under a nitroge The polymer obtained purified as described in Example It was insoluble in furan and If the of magnesium diallyl phosphate was carried out under the conditions of Bxample the polymer was virtually the same as described in the preceding Example 7 9 g of cobaltous diallyl phosphate and 1 of triallyl phosphate were copolymerized under the conditions described in Example The resultant resin was equally insoluble in common organic solvents as well as in With the teristic colour change described in Bxample 5 was Example 8 10 g of silicon diallyl phosphate in 30 ml of benzene and g of peroxide were refluxed under for five The viscosity of the solution increased 6 ethyl Example 10 g of titanium phosphate dissolved in 50 ml of containing also of benzoyl was refluxed under a nitrogen atmosphere for 10 The product obtained was washed with hydrofuran and The resinous product was insoluble in common organic solvents as well as in insufficientOCRQuality
Claims (10)
1. Solid, insoluble synthetic resins being polymers or copolymers derived from monomeric metal diallyl phosphates of the formula O Γ « i(CH2«CH.CH20)2.P-0 e I where Me is a metal having a valenoy of from 1 to 4 and may also be silicon, and n is an integer of from 1 to 4.
2. Resins according to Claim 1, wherein Me is an alkali metal (including ammonium).
3. · 3?oly( sodium diallyl phosphate).
4. Resins according to Claim 1, wherein Me is magnesium or cobalt.
5. Cobaltous diallyl phosphate-triallyl phosphate copolymers.
6. Resins according to Claim 1, wherein Me is silicon.
7. process for the preparation of diallyl phosphate polymers or copolymers according to any of Claims 1 to 6, wherein the polymerization of a diallyl phosphate of formula I in Claim 1 is effected as an initiated free-radical polymerisation.
8. A process according to Claim 7, wherein a peroxide is used as an initiator.
9. A process according to Claim 7 or 8, wherein the reaction mixture is exposed to ultraviolet irradiation in the course of the polymerization.
10. A process for the preparation of diallyl phosphate polymers or copolymers according to any of Claims 1 to 6, substantially as described herein with reference to the Examples.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2431865A IL24318A (en) | 1965-09-14 | 1965-09-14 | Metal diallyl phosphate resins and process for their preparation |
| US577125A US3441501A (en) | 1965-09-14 | 1966-09-06 | Water removal from watercontaining media |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2431865A IL24318A (en) | 1965-09-14 | 1965-09-14 | Metal diallyl phosphate resins and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24318A true IL24318A (en) | 1969-07-30 |
Family
ID=11043714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2431865A IL24318A (en) | 1965-09-14 | 1965-09-14 | Metal diallyl phosphate resins and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| IL (1) | IL24318A (en) |
-
1965
- 1965-09-14 IL IL2431865A patent/IL24318A/en unknown
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