Aromatic copolyester-sulphone ketones and synthesis method thereof

FIELD: chemistry.

SUBSTANCE: invention relates to aromatic copolyester-sulphone ketones and synthesis method thereof. Aromatic copolyester-sulphone ketones can be used as heat resistant construction materials and are compounds of general formula: : or , where m is statistical distribution of structures on the macrochain m=1-100, a n=1, 5, 10, 20. The aromatic copolyester-sulphone ketones are obtained via polycondensation of oligosulphone-ketones based on diane or phenolphthalein with diacyl chlorides of terephthaloyl-di(p-oxybenzoic acid) in 1,2-dichloroethane in the presence of double excess triethylamine.

EFFECT: obtaining aromatic copolyester-sulphone ketone, having high thermal stability and heat resistance.

2 cl, 2 tbl, 6 ex

 

The invention relates to macromolecular compounds, in particular aromatic sobolifera that can be used as a heat-resistant structural materials.

Known oligomers based on 4,4'-deoxycytidine (Diana) and 4,4'-dichlorodiphenylmethane, 4,4'-deoxycytidine and equimolar mixture of 4,4'-dichlorodiphenylmethane and 4,4'-dichlorodiphenylmethane, 3,3-di(4 oksifenil)phthalide (phenolphthalein) and 4,4'-dichlorodiphenylmethane, 3,3-di(4 oksifenil)phthalide (phenolphthalein) and equimolar mixture of 4,4'-dichlorodiphenylmethane and 4,4'-dichlorodiphenylmethane and Capoliveri based on them [1-4].

Known aromatic polyesters based bisphenola and dichlorohydrin terephthaloyl-di(p-oksibenzoynoy) acid [5].

However, the polymers are characterized by low values of thermal properties.

As the closest analogue may be used a method of producing polymers [6] the polycondensation of dichlorohydrin terephthaloyl-di(p-oksibenzoynoy) acids and diols of General formula OH-R-OH, where R is aliphatic and accelerations group composition

-(CH2)n-; -(CH2CH2O)n-; -(CH2CH(CH3)O)n-.

The disadvantages of polymers are the low values of thermal resistance and heat resistance.

The polymers are synthesized using high-temperature Busacca the priori polycondensation in an inert solvent (diphenyloxide, 200°C) in a stream of inert gas.

The disadvantages of this method are the hard conditions of synthesis: high temperature (200°C), the use of an inert gas (argon).

Object of the invention is the expansion of the range of polymers with high thermal stability and heat resistance.

The problem is solved by the fact that carry out the polycondensation of oligourethanes formula 1

where n=1-20;

or

and dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2

The invention relates to new copolymers-sopoliarilenefirketonov-di(p-oxybenzoates) (PASCHAL) General formula

where n=1, 5, 10, 20.

or

m - notation, the mean statistics (irregular) distribution of structures on macrocopy, m=1-100.

The polycondensation is carried out in chlorinated organic solvents in the presence of triethylamine at 15-25°C for 1-1 .5 hours.

The structure of synthesized copolycondensation-di(p-oxybenzoates) confirmed by elemental analysis (table 1) and IR spectroscopy.

Table 1
Elemental analysis of spoliation.
№ p/pThe polymerCalculated, %Found, %
basisCHSCHS
1USC-1D76,334,87of 2.2176,815,082,70
2RSC-5D77,72of 5.292,7877,98by 5.872,96
3USC-10D77,94are 5.362,8878,335,913,16
4USC-D78,06 5,392,9378,63by 5.873,31
5USC-1F74,81to 3.731,8775,124,111,98
6USC-5F75,633,86of 2.2675,914,342,84
7USC-F75,753,882,3276,133,962,80
8USC-20F75,823,892,3576,274,072,93
USC-D - oligocarbonate based on Diana with the degree of polycondensation n=1, 5, 10, 20.
RSC-f - oligocarbonate on the basis of phenolphthalein to the degree of polycondensation n=1, 5 10, 20.

In the IR spectra of sopoliarilenefirketonov-di(p-oxybenzoates) detected absorption bands corresponding to the vibrations of simple essential communications (930, 1015, 1045 cm-1); the oscillations of complex essential communications (1735-1750 cm-1); fluctuations isopropylidene group(1290, 1365, 1388, 1415, 1495 cm-1in the case of oligomers on the basis of Diana; the vibrations of the carbonyl group of the lactone ring cycle in the remainder of phenolphthalein (1750-1780 cm-1in the case of oligomers on the basis of phenolphthalein; fluctuations sulfonyloxy group (1150, 1170, 1215, 1245-1229, 1320 cm-1), fluctuations diarylethenes group 1600-1650 cm-1and not detected absorption bands corresponding to hydroxyl groups, which confirms the formation of the expected structure sopoliarilenefirketonov-di(p-oxybenzoates).

The feasibility of the invention is illustrated by the following examples.

Example 1. Synthesis of sobolifera based oligourethane with the degree of condensation 1 (USC-1D).

Into the reaction flask with a capacity of 250 ml, equipped with a mechanical stirrer, make 5,3865 g (0,005 mol) of oligourethane formula 1 with n=1 (based on Diana), 100 ml of 1,2-dichloroethane. With stirring, add 1,3996 ml (0.01 mol) of triethylamine and after complete dissolution of all the starting reagents in the reaction flask make equimolar quantity is of dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2, 2,2166 g (0,005 mol). The reaction is carried out for 1 hour, then diluted the resulting solution of 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol. The polymer is washed with isopropyl alcohol, and water until a negative reaction to chlorine ions and dried in vacuum at 80°C for 24 hours. The yield of copolymer was 98.0%, the viscosity of its solution in 1,2-dichloroethane at 20°C is equal to 0.60 DL/g

Example 2. Synthesis of sobolifera based oligourethane with the degree of condensation 10 (USC-10D).

Into the reaction flask with a capacity of 250 ml, equipped with a mechanical stirrer, make 17,4369 g (0.002 mol) of oligourethane formula 1 with n=10 (based on Diana), 80 ml of 1,2-dichloroethane. With stirring, add 0,5598 ml (0,004 mol) of triethylamine and after complete dissolution of all the starting reagents in the reaction flask make equimolar amount of dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2, 0,8866 g (0.002 mol). The reaction is carried out for 1 hour, then diluted the resulting solution of 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol. The polymer is washed with isopropyl alcohol, and water until a negative reaction to chlorine ions and dried in vacuum at 80°C for 24 hours. The yield of copolymer is 97.5%, the viscosity of its solution in 1,2-dichloroethane at 20°C is equal to 0.56 DL/g

Example 3. Synthesis of sobolifera based oligourethane article is singing condensing 20 (USC-D).

Into the reaction flask with a capacity of 250 ml, equipped with a mechanical stirrer, make 17,2086 g (0.001 mol) of oligourethane formula 1 with n=20 (based on Diana), 60 ml of 1,2-dichloroethane. With stirring, add 0,2799 ml (0.002 mol) of triethylamine and after complete dissolution of all the starting reagents in the reaction flask make equimolar amount of dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2, 0,4433 g (0.001 mol). The reaction is carried out for 1 hour, then diluted the resulting solution of 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol. The polymer is washed with isopropyl alcohol, and water until a negative reaction to chlorine ions and dried in vacuum at 80°C for 24 hours. The yield of copolymer is 97,0%, the viscosity of its solution in 1,2-dichloroethane at 20°C is equal to of 0.54 DL/g

Example 4. Synthesis of sobolifera based oligourethane with the degree of condensation 1 (SCD-1).

Into the reaction flask with a capacity of 250 ml, equipped with a mechanical stirrer, make 6,7372 g (0,005 mol) of oligourethane formula 1 with n=1 (phenolphthalein), 100 ml of 1,2-dichloroethane. With stirring, add 1,3996 ml (0.01 mol) of triethylamine and after complete dissolution of all the starting reagents in the reaction flask make equimolar amount of dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2, 2,2166 g (0,005 mol). The reaction is carried out for 1.5 hours, the ATEM dilute the resulting solution of 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol. The polymer is washed with isopropyl alcohol, and water until a negative reaction to chlorine ions and dried in vacuum at 80°C for 24 hours. The yield of copolymer was 98.0%, the viscosity of its solution in 1,2-dichloroethane at 20°C is equal to the value of 0.52 DL/g

Example 5. Synthesis of sobolifera based oligourethane with the degree of condensation 10 (USC-F).

Into the reaction flask with a capacity of 250 ml, equipped with a mechanical stirrer, make 21,2187 g (0.002 mol) of oligourethane formula 1 with n=10 (phenolphthalein), 80 ml of 1,2-dichloroethane. With stirring, add 0,5598 ml (0,004 mol) of triethylamine and after complete dissolution of all the starting reagents in the reaction flask make equimolar amount of dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2, 0,8866 g (0.002 mol). The reaction is carried out for 1.5 hours, then dilute the resulting solution of 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol. The polymer is washed with isopropyl alcohol, and water until a negative reaction to chlorine ions and dried in vacuum at 80°C for 24 hours.

The yield of copolymer is 97,0%, the viscosity of its solution in 1,2-dichloroethane at 20°C is equal to of 0.49 DL/g

Example 6. Synthesis of sobolifera based oligourethane with the degree of condensation 20 (USC-20F).

Into the reaction flask with a capacity of 250 ml, equipped with a mechanical stirrer, make 20,9004 g (0.001 mol) Oli is sulfonmethane formula 1 with n=20 (phenolphthalein), 60 ml of 1,2-dichloroethane. With stirring, add 0,2799 ml (0.002 mol) of triethylamine and after complete dissolution of all the starting reagents in the reaction flask make equimolar amount of dichlorohydrin terephthaloyl-di(p-oxybenzoates) formula 2, 0,4433 g (0.001 mol). The reaction is carried out for 1.5 hours, then dilute the resulting solution of 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol. The polymer is washed with isopropyl alcohol, and water until a negative reaction to chlorine ions and dried in vacuum at 80°C for 24 hours. The yield of copolymer is 97,0%, the viscosity of its solution in 1,2-dichloroethane at 20°C is equal to 0.48 DL/g

Some properties of sopoliarilenefirketonov-di(p-oxybenzoates) are shown in table 2.

Table 2
Properties sopoliarilenefirketonov-di(p-oxybenzoates)
№ p/pPolymers basedOutput %Given the viscosity η, DL/gTArt.,°CThe mass loss at T, °C
10%50%
1USC-1D98,00,60153509584
2RSC-5D98,00,58156514596
3USC-10D97,50,56161520598
4USC-D97,00,54164541615
5USC-1F98,00,52170524591
6USC-5F98,00,50175528598
7 USC-F97,00,49190530600
8USC-20F97,00,48194545619

The technical result of the invention consists in expanding the range of polycondensation sobolifera with high thermal properties.

Sources of information

1. Khanturgaeva A.M., mikitaev A.K., Shustov G.B. and other Synthesis and some properties of the block copolycarbonates based oligochlorobenyzltoluenes. - Vysokomol. Conn., 1984, t, B, No. 4, s-274.

2. Tshabalala, Laishevo, Magasumova. The heat resistance and chemical resistance of polysulfonamide. - Proceedings of the II all-Russian conference. New polymer composite materials. Nalchik, 2005, s-165.

3. Khanturgaeva A.M., Khasbulatov SS, Bajawa RC Synthesis and properties of heat-resistant aromatic block sobolifera. The journal "Izvestiya vuzov. The North-Caucasus region". Natural science, No. 3, 2007, p.50-52.

4. Zinaida S.Khasbulatova, Luiza A.Asuyeva, Madina A.Nasurova, Arsen M.Kharayev, Gennady B.Shustov. Polysulfonetherketones on the Oligoether Base, Their Thermo - and chemical Resistance. Polymers, Polymer Blends, Polymer Composites and Tilled Polymers Synthesis, Properties and Aplications, New-York, 2006

5. Andreev, L.N., Bushin SV, Matyushin A.I., Bezrukova M.A., Flowers, VN, Bilibin, A., Skorokhodov S. Hydrodynamic, diamoutene and conformational properties of the molecules are para-aromatic polyester containing small additive m-venereologia cycle. Polymer sciense ser. Conn., 1990, volume 32, No. 8, s-1759.

6. Bilibin A. Y., Shepelevskii A. A., Savinova I.e., Skorokhodov S. Avts No. 792834 the USSR, IPC C07C 63/06, C08K 5/09, BI No. 12.

1. Aromatic depoliticalization General formula:

where n=1, 5, 10, 20,
; or
m - notation, the mean statistics (irregular) distribution of structures on macrocopy m=1-100.

2. A method of producing polymers according to claim 1, which consists in the fact that dissolve oligocarbonate based on Diana or phenolphthalein with the degree of polycondensation of 1, 5, 10, 20 1.2-dichlorethane and with stirring, add double the excess triethylamine in relation to the oligomer, after complete dissolution of all of the source reagents are added equimolar amount of dichlorohydrin terephthaloyl-di(p-oksibenzoynoy) acid and carry out the polycondensation in for 1-1 .5 h at a temperature of 15-25°C. the resulting solution was diluted with 1,2-dichloroethane and the polymer precipitated in isopropyl alcohol, washed with water until a negative reaction to chlorine ions and dried in the Aquum at 80°C.



 

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