DE2032566B2 - 4-CAPROYLBENZOIC ACID-4'-ALCOXYPHENOLESTER AND NEMATOGENIC MIXTURES CONTAINING THESE - Google Patents

Description

wherein R is an ethyl or a butyl radical.

2. Containing nematogenic mixture

a) 4-Caproyloxybenzoic acid-4'-ethoxyphenol ester (I) or 4-caproyloxybenzoic acid-4'-butoxyphenol ester (II),

b) N - (4 - methoxybenzylidene) - 4 '- O - η - butyrylaminophenol (III),

c) 4-methoxybenzylidene-4'-n-butylaniline (IV) or 4-ethoxybenzylidene-4'-n-butylaniline (V). ^ao

3. Nematogenic mixtures according to claim 2, containing the compounds (I) or (II) and (III) and (IV) or (V) in a molar ratio of 1 part I or II: 2 parts III: 2 parts IV or V. a ₅

Il

C ₅ H ₁₁ -CO-

-COO-

-0-R

the addition of which the clearing point of the abovementioned compounds IV and V is increased. A mixture of 2 mol IV and 1 mol III has a clearing point of 70 ^° C., which is about 30 ^° C. higher than that of the pure compound IV. However, the melting point of the mixture is hardly below that of the pure compound (IV). However, it has also been found that nematic mixed phases with melting points below ⁰ ° C. are obtained if 4-caproyloxybenzoic acid-4'-ethoxyphenol ester is used as the third component

The invention relates to 4-caproylbenzoic acid-4'-alkoxyphenol esters the general formula

35

CH ₃ O

CH = N

Il

OC-C ₃ H ₇

CH ₁₁ -CO

COO-

-OC ₂ H ₅

or 4-caproyloxybenzoic acid-4'-butoxyphenol ester of the formula

C ₅ H ₁₁ -CO-

-OC ₄ H, (H)

wherein R is an ethyl or a butyl radical.

The invention also relates to nematogenic mixtures which are composed of one of the aforementioned compounds, N- (4-methoxybenzylidene) -4'-O-n-butyrylaminophenol and 4-methoxy- or 4-ethoxybenzylidene-4'-n-butylanine exist.

The subject of the earlier German patent (patent application P19 28 242.9) are the azomethines 4-methoxybenzylidene-4'-n-butylaniline (IV) and 4-ethoxybenzylidene-4'-n-butylaniline (V), the enantiotropic nematic phases at room temperature little or form about it and whose nematic phases have Persistenzbereiche ⁰ C from 20 to 3O. Especially in the 4-methoxy-benzyIiden-4'-n-butylaniline with a melting point of 20 ⁰ C and a clearing point of about 42 ⁰ C is the first time a connection before that allows working with nematic liquid without extensive temperature slightly above the normal room temperature .

However, it is advantageous to use nematic liquids with an even lower melting point and more To have persistence range available so that thermostatting can be dispensed with entirely.

In the compound N- (4-methoxybenzylidene) -4'-O-n-butyrylaminophenol the formula

clogs. These connections are new. They are nematogenic themselves.

1 was made as follows:

49.3 g of 4-caproyloxybenzoyl chloride, dissolved in 250 ml of benzene, were treated with a solution of 21 g of 4-hydroxyphenetol in 300 ml of benzene. 15 ml of pyridine in 100 ml of benzene were added dropwise to this solution. The reaction mixture was then refluxed for 3 hours. After cooling, the pyridine hydrochloride formed was filtered off. The benzene solution was then washed with dilute sodium hydroxide solution and then with water, dried over sodium sulfate, and the benzene was distilled off. The distillation residue was recrystallized from hexane. 4-Caproyloxybenzoesäure-4'-äthoxyphenolester melts at 64-65 ⁰ C to a nematic melt whose clearing point is 100-101 ⁰ C.

II 59 is obtained analogously from 4-Caproyloxybenzoylchlorid and 4-Hydroxyphenolbutyläther mp. To 6O ⁰ C, cl.p.. 89 to 90 ^° C. (from hexane).

The mixtures with the lowest melting points and the widest persistence ranges of the nematic liquid are made up of

2 moles of compound IV]

2 mol of the compound III \ mp. -3 ⁰ C, KIp. + 8O ⁰ C.

1 mole of compound I J

2 moles of compound IV 1

2 mol of the compound III \ mp. -2 ° C, KIp. +75 ⁰ C.

1 mole of compound II J

Likewise, a melting point below 0 ⁰ C, albeit a narrower persistence range, shows z. B. a mixture of

3 moles of compound IV )

2 moles of the compound HI | Mp. -3 ⁰ C, KIp. +62 ⁰ C. 1 mole of compound IJ

In the case of mixtures with V, the melting points (HI) 65 are naturally higher.

A major advantage of the new nematogenic mixtures is their stability. You don't tend to a mixture component was found, through crystallization or separation. You can

can be mixed with relatively large amounts of dissolved foreign matter without affecting the nematic character is lost, ζ. B. with up to 9% benzene. They have a pronounced »dynamic scatterings effect, and they are well suited as solvents for nuclear magnetic resonance spectroscopy.

Claims (1)

Patent claims: 1. 4-Caproyloxybenzoic acid-4'-alkoxyphenol ester of the general formula C ₅ H ₁₁ -CO- -COO 0-R