SU1216187A1 - (2-h-nonylimidazodazolyl-1-diethyleneamino) amide of o-h-octyl-4-oxy-3,5-di-tert-butylthiophosphonic acid as ageing inhibitor for butadiene-styrene rubber - Google Patents

Description

This invention relates to the chemistry of phosphonic KHCJioTbi derivatives, namely, to a new (2-n-1H1-imidazolyl-1-diethylenamino) amide 0-H-octyl-4-hydroxy-3,5-di-tert-butyl thiophosphonic acid of the formula

-9Н2

x} -С2Н -Ш1гС2Н1Г Н-Р

K-CgHia

ys #.

which can be used as a butadi-aging inhibitor. styrene rubbers.

Example. Preparation of (2-n-nano-imidazolyl-1-diethylenamino) amide of 0-n-octyl-4-hydroxy-3,5-di-ter-butyl-tiophosphonic acid 22.5 g (0.075 mol) of 4-hydroxy anhydride -3,5-di-t.v.-butylphenyldithiophosphonic acid is dissolved by heating in 200 MP of p-xylene. To the resulting solution was added 20.9 g (0.075 mol of 1-diethylenediamine-2-non-1-imidazoline in 50 MP I-xylene. The reaction was carried out in a three-necked flask with reflux condenser, stirrer and thermometer

dissolve at boiling temperature

L for 6 hours. 8 Mp (0.075 mol) of H-octyl alcohol is added to the dithiophosphonic acid monoamide obtained, the reaction mixture is boiled for 4 hours until the release of hydrogen sulfide is stopped. After completion of the reaction, the solvent was distilled off in vacuo. In the residue, a viscous, dark-colored, resinous substance is obtained, which is recrystallized from the chloroform-heptane system. The resulting product is lemon-colored crystals. The product yield 43 g (81%).

Found,%: C 69.45; H 9.98; N 7.63; P 4.12.

Calculated,%: C 69.9; H 9 | eleven; N 7.41; R 4.3. |

In the IR spectra of the product are doubled from the absorption band, characteristic for the stretching vibrations of the following groups: 1615-1690, 1500-1600, 1652- 1662, 3300-3400, 2915-2940, 1585, 560 and 3500-3600 groups C

five

0

(five

0 5

0

S.-C-C, -N-N, -CH, C (arom) -O; C (alif) -6; P-S, -OH, respectively.

 cryosk 0 U Compound (I) investigated on

inhibitory activity during thermal oxidation of styrene-butadiene rubber. In parallel, the known 0,0-di-H-nonyl-3,5-di-H-octyl-I-hydroxybenzylphosphonate (II) and the industrial inhibitor phenyl-3-naphtylamine (naphtham-2) (III) were investigated.

Example2. In Butadiene rubber, purified from an industrial inhibitor by extraction with ethanol from a toluene solution, compound (I) is introduced at a concentration of 0.5; one; 1.5; 2 places on 100 ma.ch. rubber Films are prepared from the solution. In a special thermal-oxidative installation, the films are held in air at 130 ° C for 140 minutes, at-60 minutes, at-30 minutes, and at 180 ° C, 8 minutes. The films are then dissolved in toluene. The characteristic viscosity is measured and the molecular weight of the rubber is determined by the formula

t KM.

The aging factors for the preservation of the molecular mass of rubber are determined by the formula

35

TO.

. Mg

where M is the molecular weight of the original rubber;

M-, is the molecular weight of the oxidized rubber at different temperatures.

The results of the comparison of the effectiveness of inhibitors of aging of butadiene styrene rubber are given in the table.

As follows from the table, compound (1) is a highly effective inhibitor over the entire specified temperature range, especially at high temperatures. When the inhibitory activity of compound (I) is 3-4 times higher than in the known ones.

11216187

Conservation factor mol.m. rubber with inhibitors

I

T.S.

Connection 1P

Compound II

1.5 I 2.0 1.5 I 2.0 I 0.5 1, oJ 1.5 J, 2.0

0.68 0.45 0.32 0.31 0.20

0.7

0.6

0.4

0.35

0.21

Compiled by L.Karunina Editor N.Rogulich Tehred A.AchCorrector T.Kolb

Order 960/28 Circulation 343Subscription

VNIIPI State Committee of the USSR

for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5

Branch PPP Patent, Uzhgorod, Proektna St., 4

I

Compound I

Inhibitor Concentration,%

0.6

0.38

0.32

0.27

0.21

0,60,650,680,72

0,660,690,710,75

0,680,700,740,79

0,690,710,750,78

0,670,700,700,73

Claims (1)

<claim-text> <table border = "1"> <tbody> <tr> <td colspan = "4"> 'Conservation factor mol. rubber </ td> <td colspan = "5"> with inhibitors </ td> </ tr> <tr> <td> T, ° C </ td> <td colspan = "2"> Connection ΙΗ 1 </ td> <td colspan = "2"> Compound II. </ Td> <td> I </ td> <td colspan = "3"> Compound I </ td> </ tr> <tr> <td> </ td> <td> </ td> <td> </ td> <td colspan = "2"> Concentration </ td> <td> inhibitors, </ td> <td> Ζ </ td> <td> </ td> <td> </ td> </ tr> <tr> <td> </ td> <td> 1.5 | </ td> <td> 2.0. | </ td> <td> <sup> 1.5 </ sup> 1 </ td> <td> 2.0 </ td> <td> | 0.5 </ td> <td> I '&gt; ° | </ td> <td> 1.5 </ td> <td> 2.0 </ td> </ tr> <tr> <td> 130 </ td> <td> 0.68 </ td> <td> 0.7 </ td> <td> 0.5 </ td> <td> 0.6 </ td> <td> 0.6 </ td> <td> 0.65 </ td> <td> 0.68 </ td> <td> 0.72 </ td> </ tr> <tr> <td> 140 </ td> <td> 0.45 </ td> <td> 0.6 </ td> <td> 0.31 </ td> <td> 0.38 </ td> <td> 0.66 </ td> <td> 0.69 </ td> <td> 0.71 </ td> <td> 0.75 </ td> </ tr> <tr> <td> 150 </ td> <td> 0.42 </ td> <td> 0.4 </ td> <td> 0.29 </ td> <td> 0.32 </ td> <td> 0.68 </ td> <td> 0.70 </ td> <td> 0.74 </ td> <td> 0.79 </ td> </ tr> <tr> <td> 160 </ td> <td> 0.31 </ td> <td> 0.35 </ td> <td> 0.25 </ td> <td> 0.27 </ td> <td> 0.69 </ td> <td> 0.71 </ td> <td> 0.75 </ td> <td> 0.78 </ td> </ tr> <tr> <td> 180 </ td> <td> 0.20 </ td> <td> 0.21 </ td> <td> 0.17 </ td> <td> 0.21 </ td> <td> 0.67 </ td> <td> 0.70 </ td> <td> 0.70 </ td> <td> 0.73 </ td> </ tr> </ tbody> </ table>