Organocobalt complexes with tridentate schiff's bases as initiators of emulsion polymerization and copolymerization of diene and vinyl monomers

FIELD: organometallic polymerization catalysts.

SUBSTANCE: invention relates to alkylcobalt(III) complexes with tridentate Schiff's bases wherein alkyl ligand contains functional group, notably hydroxyl, carboxyl, or amino group, in accordance with general formula:

(I),

in which W represents two-moiety unsaturated hydrocarbon bridge group expressed by formula =C(H)=C(CH3)- (propene-1,2-diyl) or o-C6H4 (o-phenylene); X is OH, NH2 or COONa; Y monovalent anion: Cl-, Br-, NO3- or ClO4-; and Z polymethylene bridge group (CH2)n, wherein n=3-11 when X = OH or NH2 and n=2-11 when X = COONa. The complex are used as initiators of emulsion polymerization and copolymerization of diene and vinyl monomers to produce reactive bifunctional oligomers and polymers with terminal functions, which oligomers and polymers are suitable for further conjugation with corresponding reagents.

EFFECT: extended choice of specific polymerization catalysts.

3 tbl, 30 ex

 

The invention relates to the fields of chemistry of ORGANOMETALLIC compounds and polymers, namely complexes alkylate(III) with tridentate Schiff bases, in which the alkyl ligand contains functional, namely hydroxyl, carboxyl or amino group, and the use of these complexes as initiators for emulsion polymerization and copolymerization of diene and vinyl monomers to obtain a reactive bifunctional oligomers and polymers with end groups.

Introduction to polymer functional groups can be used for immobilization of biologically active compounds, such as obtaining immunodiagnostics and grafting catalysts (Hartley F. Anchored metal complexes - a new generation of catalysts. M.: Mir, 1989), as well as to modify the properties of the polymer. Received likewise a bifunctional oligomers can serve as the starting substances (components) for polycondensation (co)polymers.

Still using for this purpose the method of emulsion polymerization as the initiators used appropriately functionalized peroxide and azo compounds (Ivanchev S.S., USP, 1991, 60, 1368-1390). However, in this case, the process have to spend at elevated (>60° (C) the erature and relatively high concentrations of initiator. The latter leads to the fact that the number of functional groups on the surface of the polymer particles is much greater than optimal. The result is lyophilization surface and, consequently, decreases the stability of these particles in saline solution when the use of such suspensions as carriers of bioligands. On the contrary, in the case of the proposed use of the initiators it is possible to control the number of functional groups on the surface of the particles by varying the initiator concentration.

Know the use of complexes of alkylate(III) with tridentate Schiff base - alkyl{2-[(2-amino-ethyl)imino]-3-alkyl-Penta-3-EN-4-OST}-(1,2-amandemen)cobalt(III) bromide (I, where XZ is simple, i.e. not functionally substituted alkyl group, a CnH2n+1and Y=Br) as initiators for emulsion polymerization (patent RF №2070202, 1991). These compounds are highly efficient initiators for emulsion polymerization, operating at room and even lower temperatures; however, they do not contribute to the composition of the polymer functional groups.

The objective of the invention was to obtain new high-performance low-temperature emulsion polymerization initiators containing an initiating radical is hydroxyl, carboxyl or amino group, which approach the Yat for the subsequent conjugation of the resulting polymers with appropriate reagents.

This problem is solved by the new structure of the complexes (functionally substituted alkyl)cobalt with tridentate Schiff bases of General formula I

where W is the two-tier bridge unsaturated hydrocarbon group, namely S(N)=C(CH3)- (propene-1,2-diyl, A), or o-C6H4(o-phenylene, C), X=OH, NH2or COONa, Z is a saturated hydrocarbon bridge, namely polymethene ((CH2)ngroup, and Y is a singly charged anion, namely CL-, VG-I-, NO3-or ClO4-. So far complexes alkylate with tridentate Schiff bases containing alkyl ligand functional groups, were not known.

Comparative analysis with analogues leads to the conclusion that provides connection of the new structure. Thus, the claimed technical solution meets the criterion of “novelty”.

These complexes (ω -hydroxy-n-alkyl)-, (ω -amino-n-alkyl) -, and [ω -(sodium carboxylate)-n-alkyl]{2-[(2-amino-ethyl)imino]Penta-3-EN-4-olato} - (2-{ 1-[(2-amino-ethyl)imino]ethyl}phenolate)(1,2-amandemen)cobalt(III) bromide *, chlorides, iodides, nitrates and perchlorates (symbolic formula [X(CH2)nWith(assep)(EP)]Y (IA) and [X(CH2)nCo(7-Me-salen)(en)]Y (IB), respectively) for the first time obtained by the authors, as the op is Sano below.

Complexes I bromidum the counterion (Y=Br) and X=HE, COONa, Sh** synthesized template method, mainly by analogy with published methods obtain the corresponding complexes with simple, i.e. functionally unsubstituted alkyl ligands CnH2n+1namely complexes rows [RCo(acacen)(en)]Br (RF patent 2070202, 1991) and [RCo(7-Me-salen)(en)]Br (I.Ya. Levitin et al., Inorg. Synth. (S. Kirschner, ed.), Wiley, New York, 1985, V.23 supported, pp.163-171), under anaerobic conditions and with constant stirring. Complexes with other counterions (Y=Cl, I, NO3, ClO4) received from the corresponding bromides by ion exchange reactions in solutions, by analogy with complexes with simple alkyl ligands (I. Ya. Levitin et al., Inorg. Chim. Acta, 1985, 100, 65-77). Complexes if possible, protected from light during all operations and kept in the dark. Evaporation of the solutions were carried out in a vacuum at a bath temperature not exceeding 30° C.

The complexes identified and characterized using elemental analysis (table 1 *), PMR, IR and electronic spectroscopy, as well as TLC and capillary electrophoresis. Their exits and chromatographic characteristics are shown in table 2.

* and (ω -bromo-n-alkyl){2-[(2-amino-ethyl)imino]Penta-3-EN-4-olato} - (2-{1-[(2-amino-ethyl)-imino]ethyl}-phenolate)(1,2-amandemen)cobalt(III) bromide ([Br(CH2)nCo(acacen)(en)]Br and [Br(CH2)nCo(7-Me-salen)(en)]Br), which is s are intermediates in the synthesis of the corresponding ω -aminosilane complexes

** see previous note

* there is given the numbering of complexes

Option (I): Obtaining 6-hydroxyhexyl{2-[(2-amino-ethyl)imino]Penta-3-EN-4-OST}(1,2-amandemen)-cobalt(III) bromide ([(CH2)6With(assep)(EP)]VG, No. 4).

A solution of acetylacetone - 3.08 ml (30 mmol) and Ethylenediamine - 2.01 ml (30 mmol) in methanol (110 ml) was kept up until he not turned yellow. Then added l2·6N2About - 3.6 g (15 mmol). To the resulting brown solution while cooling water is gradually covered caustic soda - 3.7 g (80 mmol); the solution turned into a carrot-red suspension. After dissolving caustic soda water bath was heated to 25° C. Then added a 2%solution of PdCl2in 1 M KCl aqueous solution of 0.3 ml and 2.94 ml (to 22.5 mmol) 6-Bromhexine. Then the reaction flask was protected from light. Then addedl/10part of the solution of 0.8 g (20 mmol) NaBH4in a solution of 0.4 g (≈ 10 mmol) of NaOH in 5 ml of methanol. The remaining solution was added gradually over 5 hours. After this I continued to stir the reaction mixture under anaerobic conditions for another hour. Then it was cooled for several hours at 0° C. the precipitation was Filtered and washed it on the filter with methanol up until the wash liquid has not ceased to be painted. The wash liquid with denile with liquor. The resulting solution was concentrated in vacuo to 30 ml and left to crystallize at 0° C. the precipitate dark red color separated by filtration and dried by suction on the filter. Then washed it CH2CL2up until the rinsing liquid is stopped painted in green color. Remaining on the filter product red was dried by suction on the filter and finally in vacuum over calcium chloride. Product raw was purified by recrystallization from methanol. Allocated thus the complex is a red crystalline powder.

Similarly got other complexes of a number of [HO(CH2)nCo(acacen)(en)]Br (No. 1-3, 5, 6). The outputs from 80% (n=3) to 55% (n=11) - see table. 2.

Option (2): Getting 5-aminoallyl{2-[(2-amino-ethyl)imino]Penta-3-EN-4-OST}-(1,2-amandemen)cobalt(III) bromide ([(CH2)5With(assep)(EP)]VG, No. 13).

a - Synthesis of the corresponding ω -romancelanguage complex ([Br(CH2)5Co(acacen)(en)]Br, No. 12).- The synthesis was performed in analogy with the synthesis of 1, with the difference that as alkylating means instead of 6-Bromhexine used the 1.5-dibromethane (6.13 ml, 45 mmol). The obtained intermediate product is a red crystalline powder.

b - Amination received ω -romancelanguage complex.-[Br(CH2 )5Co(acacen)(en)]Br (0.5 g) was dissolved in concentrated aqueous ammonia solution (70 ml). The resulting solution was left to stand at room temperature; the reaction course, which ended after 3 hours, monitored by TLC under the conditions listed in table. 2. After addition of Na2CO3(0.5 g) and the resulting solution was concentrated in vacuo, and then was extracted with dichloromethane. The extract was dried over Na2SO4and concentrated in vacuum. Product landed ether, filtered and dried on the filter. Received a red crystalline powder.

Options (3,4): Obtain 2-(sodium carboxylate)ethyl - 5-(sodium carboxylate)amyl{2-[(2-amino-ethyl)-imino]Penta-3-EN-4-OST}(1,2-amandemen)-cobalt(III) bromide ([NaOCO(CH2)nCo(acacen)(en)]Br, n=2, 5; No. 15 and 16).

The synthesis was performed in analogy with the synthesis of 1, with the difference that as alkylating means instead of 6-Bromhexine used a methanol solution of 3-bromopropionate and 6-bromopropane sodium, respectively. They were prepared by adding to a cooled and stirred solution of 3-bromopropionate and 6-bromophenol acid (22.5 mmol - 3.44 and 4.39 g, respectively) Na2CO3to stop gassing; the excess reagent was removed by decantation. The products are red crystalline powder.

Option (5): 11-hidroxi the decyl(2-{1-[(2-amino-ethyl)imino]-ethyl}phenolate)(1,2-amandemen)cobalt(III) bromide ([HO(CH 2)11Co(7-Me-salen)(en)]Br, No. 19).

The synthesis was performed in analogy with the synthesis of 1, with the difference that as ketoenol and alkylating means instead of acetylacetone and 6-Bromhexine used on-hydroxyacetophenone (3.61 ml, 30 mmol) and 11-bromoundecane (5.65 g - 22.5 mmol), respectively. The product is a red crystalline powder.

Option (6) 11-(sodium carboxylate)undecyl(2-{1-[(2-amino-ethyl)imino]ethyl}phenolate)-(1,2-amandemen)-cobalt(III) bromide ([HO(CH2)11Co(7-Me-salen)(en)]Br. No. 22),-

The synthesis was performed in analogy with the synthesis of 5, with the difference that as alkylating means instead of 11-bromoundecanoic used a methanol solution of 11-bromoundecanoic sodium, prepared by adding to a cooled and stirred solution of 11-bromoundecanoic acid (5.97 g - 22.5 mmol) of Na2CO3to stop gassing; the excess reagent was removed by decantation. The product is a red crystalline powder.

Option (7): Obtain 6-hydroxyhexyl{2-[(2-amino-ethyl)imino]Penta-3-EN-4-OST}(1,2-amandemen)cobalt(III) chloride ([(CH2)6With(assep)(EP)]CL, No. 8).

To an almost saturated solution of [(CH2)6With(assep)(EP)]VG (t - 2.5 mmol) in methanol was added dropwise a saturated aqueous solution bl2(0.35 g - 1.25 mmol). After separation by decantation obrazovash is gosia sediment (br 2to the resulting solution was added twice the amount of cold water and it evaporated in a vacuum to the onset of crystallization. Was finally led at 0° C. the Precipitated product was separated by filtration, washed with a small amount of ice-cold water and dried on the filter. Received a red crystalline powder, yield 82%.

Similarly, on the basis of the respective complexes I, Y=Br, received and other complexes with chloride counterion I, Y=CL(№7, 17, 20).

Option (8): Obtain 6-hydroxyhexyl{2-[(2-amino-ethyl)imino]Penta-3-EN-4-OST}(1,2-amandemen)-cobalt(III) iodide ([(CH2)6With(assep)(EP)]I, No. 10).

A nearly saturated solution of [HO(CH2)6Co(acacen)(en)]Br (1 g) in methanol is added to a saturated aqueous solution (5 ml) of NaI. The precipitated product was separated by filtration, washed with a small amount of ice-cold water and dried on the filter. Got dark red crystals, yield 85%.

Similarly, on the basis of the respective complexes I, Y=Br and accordingly NaClO4or NaNO3(instead NaI), received the complexes with perchlorate and nitrate counterions I, Y=lO4and NO3(No. 9 and 11, 18, 21).

Examples of the synthesis of polymers in the presence of complexes I are given below. The initiators are listed under the numbers given in the table. 1.

Example 1 (invention)

In the reactor with stirrer mix 100 wt. hours of purified styrene double reconcretion under vacuum, with a water phase comprising 4 wt. including alkylsulfonate sodium (E-30) with the length of alkyl substituent C15the initiator No. 9, and 200 wt. including water. The process is carried out under stirring in nitrogen atmosphere at a temperature of 40° and pH equal to 7, for 5 hours to a conversion of 97%. The polymer contains 0.01 wt.% groups HE-.

Examples 2-7.

Perform analogously to example 1, by changing the type of monomers, initiators, emulsifiers, temperature, pH and concentration of ingredients.

Example 8 (comparative)

In the reactor with stirrer mix 100 wt. including styrene, purified double reconcretion under vacuum, the aqueous phase comprising 4 wt. including alkylsulfonate sodium (E-30) with the length of alkyl substituent With15the initiator, consisting of 0.11 wt. including complex with actinium Deputy and 200 wt. including water. The process is carried out under stirring in nitrogen atmosphere at a temperature of 20° and pH=7 for 5,0 hours to a conversion of 94%. The polymer does not contain functional groups.

The recipes and the results of the use of complexes I as initiators for emulsion polymerization are shown in table 3.

The presence of polystyrene, obtained by initiating the polymerization of complexes I, X=OH or NH2Z=(CH2)5and Y=Br, functional groups containing a mobile hydrogen atom was proved by fluorescent analysis is, when used as a label fluoresceinisothiocyanate.

To increase the content of functional groups in the polymer can be introduced in the reaction mixture, the molecular weight regulator. the pH of emulsion systems support through a known buffer systems.

Complexes of organocobalt with tridentate Schiff bases of General formula I

where W is the two-tier bridge unsaturated hydrocarbon group, namely S(N)=C(CH3)-(propene-1,2-diyl) or o-C6H4(o-phenylene);

X (functional group) - HE, NH2or COONa;

Y is a singly charged anion, namely CL-, VG-I-, NO3-or ClO4-,

Z is a saturated hydrocarbon bridge, namely polymethene, (CH2)nthe group, where the number of links n=3-11, if X=OH or NH2and n=2-11, if X=COONa;

as initiators for emulsion polymerization and copolymerization of vinyl and diene monomers.



 

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