SU1499895A1 - 1-(2,3-epoxypropyl)-3-(2,3-epithiopropyl)-benzimidazolone-2 as monomer for heat-proof glue compositions - Google Patents

Abstract

The invention relates to derivatives of heterocyclic substances, in particular 1-

Description

This invention relates to the chemistry of heterocyclic sulfur compounds, specifically to a new chemical compound, 142.3-epoxypropyl) -3- (2,3-epitiopropyl) -benzimidazolone-2, of the formula

which can be used as a monomer for heat resistant adhesives.

The purpose of the invention is the discovery of a new monomer based on the benzimmdazolone-2 system, which provides a higher heat resistance of polymer adhesives than the analogue in structure

and the appointment of 1,3-diglycidylbenzimide zolone-2 (li).

PRI me R. In a round bottom flask equipped with a stirrer, 24.6 g (0.1 mol) of 1,3-diglycidylbenzimidazolone-2, 7.6 g (0.1 mol) of thiourea and 400 ml of methanol are placed. The mixture is stirred at room temperature for 5 hours. Then the insoluble / 1 precipitate of the diepoxide compound is filtered off 1 l) t, the filter is evaporated in vacuo at room temperature. The resulting viscous resin, containing mainly compound I m of a small amount of unreacted zpoxide II, is treated three times with ether to separate the latter, each time pouring the extract into a common container. The resulting ethereal monomer solution is evaporated in vacuo and 5.5 g (21%) are obtained.

,

Yu

1- {2,3-epoxypropyl) -3- (2.3-epitiopropyl) -benzimidazolone9-2. m.p. 70-72 ° C (from a mixture of hexane and isopropanol, 10: 1). Rf 0.85 (in a mixture of chloroform and methanol, 10: 1).

Found.%: C 59.5; H 5.6; N 10.7; S 12,0.

Cl3Hl4N202S.

Calculated,%: C 59.5; H 5.3; N 10.7; S 12,2.

The table shows the comparative data of the properties of adhesive based on monomer I mixed with ED-20 resin, compound II mixed with ED-20 and III resin (base object) (ED-20 resin) with diethylene-triamine as a hardener.

As can be seen from the presented data, the proposed compound I even in an amount of 40% by weight of the entire epoxy component (mixed with monomer III) provides a significantly higher heat resistance of the adhesive composition than in the case of joining E and III (glass transition temperature of 160 ° C against 115 ° C for I and 108 ° C for III) with approximately equal or even greater strength characteristics of the polymer adhesive layer. Especially important is the preservation of adhesive strength (grandfather) at high temperatures (150 ° C), which is not observed

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neither in the case of compound II nor in the case of monomer III.

Thus, the use of 1- {2,3-epoxypropyl) -3- (2,3-epitiopropyl) -benzimidazolone-2 provides a higher heat resistance of adhesive compositions with diethylenetriamine 8 as a hardener compared to its analogue in structure and purpose (glass transition temperature versus), in addition, adhesive compositions based on the proposed compound with an increase in temperature from room temperature to slightly change the adhesion strength (ddv varies from 13.5 to 10.4 MPa), while in the case of the analogue the structure and purpose of these changes is quite bulky (about 3-4 times).

The formulas of the invention 1- (2,3-Epoxypropyl) -3- (2,3-epitiopropyl) benzimidazolone-2 of formula

as a monomer for heat resistant adhesives.

Heat resistance and physical and mechanical properties of adhesive compositions based on 1- {2,3-zpoxypropyl) -3- (2,3-epithiogfopml} -benzimmdazoloia-2 (I), 1,3-Aiglicidilbenzimidazolone-2 (II) and diglP1tsadmlovy ether bmsphenol A (III)

Note. In all compositions, the amount of cured (spruce (diethylenetriamine) was 10 May. Parts per 100 parts by weight of epoxy component; the mass ratio of monomers I and (11, H and III in both cases x 2: 3 Day + 200 ° C / 1 h.

Claims (1)

Claim 1- (2,3-Epoxypropyl) -3- (2.3-epithiopropyl) benzimidazolone-2 formulas as a monomer for heat-resistant adhesives. '' Heat resistance and physical and mechanical properties of adhesives based on 1- (2,3-epoxypropyl) -3- (2,3-epithioproml) -benzimmdazolone-2 (I), KZ ^ Diglycidylbenzimidazolone-2 (II) and diglycidyl ether of bisphenol A (III) Epoxy component Adhesion Strength, MPa Glass transition temperature with uniform separation. shear d _C dv room temperature room temperature . 150 ° C Ι + ΙΙΙ 30.5 13.5 10,4 160 11 + 111 30,0 13.0 4.3 ' 115 III 28 12.0 3.6. . 108 Note. In all compositions, the amount of hardener (diethylene triamine ' was May 10th. hours per 100 parts by weight epoxy component; the mass ratio of monomers I and III, II and III in both cases is 2: 3. The curing mode of all compositions days + 20 ° C / 1 h. · ^?