SU594096A1 - 4,4'-bis(p-aminophenyl) ester of tetrafluorohydroquinone as monomer for obtaining heat-resistant polymers - Google Patents

Description

The invention relates to a novel aromatic diamine, in particular, to 4,4-bis "(P: -aminophenyl) ether tetrafluorohydrochic, which can be used as a monomer for the production of heat-resistant polymers, in particular, heat-resistant polyamides. The proposed tetrafluorohydroquinone ester has the following formula:

F f

Zh Vo - // Vo A

NHg

F f

Diamics such as m-phenylenediamine or fluorine-containing aromatic diamines 2J, are used to produce: polyamides. However, the thermostability of such polyamides is not high enough.

To expand the range of diamines used to obtain heat-resistant polymers, a 4,4-bis- (p-aminophenyl) ether of tetrafluorohydrohyinone of formula I has been proposed,

4,4 -bio-amyrophenyl) e4ir of tetrafluorohydroquinone of formula I is obtained by reduction of the corresponding 4,4-by-b (p-nitrophenyl) ether; The desired product is isolated in a yield of 7% of theoretical. ,

For example, To a mixture of 5 g of tin and 17 ml of hydrochloric acid (dLl, 19) is added a suspension of 2.5 g of tetrafluorohydroquinone 4,4-bis- (p-nitrophenyl) ether of tetrafluorohydroquinone in 50 ml of ethanol. Then the reaction mixture was boiled for 24 hours, cooled. 25 ml of 50% potassium hydroxide is added. The precipitate is filtered off, washed with water, dried | and crystallized from benzene. Yield 1.54 g (7O%) j m.p. 184-186 With,

Found about.%: C 59.17; 59.24; H 3, 38 F 2O, 73G2O, 90; -Nl 7.59; 7.79 ..

C, gHi2 F + f aOaCalculated,%: C 59.34; H 3.29j F 20.87 ;: N 7.69.

Polyamides based on diamine of formula 1 possess a complex of valuable properties:

high thermal and frost resistance, non-flammability and the ability to easily turn into films.

O) Aviation of the properties of polyamides from the acid isofta and m-phenylenediamine or kev of fluorine-containing aromatic diamines with the properties of polyamides from iophthalic acid and tetrafluorohydroquinone ether are listed in Table 1 and 2.

Therefore, the proposed diamine allows to obtain polyamides with better properties than the known ones.

Table 1

 m-phenylenediamine

360 fluoride

F F F F

{Comparative)

Claims (2)

1. Information VNIISV. Chemical fiber, No. 6, 1968, p. 72. 2. L Alichenko B., F. et al. The Effect of Fluorine Atoms on the Properties of Polyamides. High Molecular Compounds, A13.8O9, 1971.