SU1409630A1 - 2,4,6-tris-/4ъ-carboxylatophenoxy-(2",4",6"-tris-dimethylaminomethyl-1"-oxyphenyl)/1,3,5-triazine as hardening agent of epoxydian resin and glue composition based thereon - Google Patents

Abstract

The invention relates to trimesins, in particular 2,4,6-trisE; 4 -carboxylate-phenoxy- (2, 4, tris-dimethylaminomethyl-1-oxyfenyl-1,3,5-triazine (ST)), which can be used as a hardener of epoxy sidian resin in an adhesive composition The goal is to create a more effective hardener that increases the viability of the adhesive and bonding strength. Synthesis of ST is a 2,4,6-tris reaction

Description

114096302

The invention relates to the field of 2,4, 6-tris-4 -carboxylate derivatives of the simm-triazinsoder- (2,4,6 -tris-dimeshsaminaminomethyl-1) derivatives of carboxylic acids, specifically coxiphenyl) 3-1,3,5-triazine of the formula:

rillt

., /.-CH.NlCHs), COONHCHi-fVoH

CHjNlCHslz

CHj

CHjHjIoOC

CHj

CH.NlCHs), oH

CHjNlCHslz

CHiNlCHsb. OH

CHjN (CH3) 2

which can be used as a hardener for epoxy diane, as well as for glue based on epoxy diane resin and this hardener, with the following ratio of components w.h.: epoxy diane 100,0, triazine-containing hardener 11,5- 23.0, which can be used for bonding metals and plastics.

The aim of the invention is to obtain a new hardener based on simm-triazine-containing tricarboxylic acid, the use of which in the composition of an adhesive based on epoxy diane resin would increase the adhesive strength and increase the viability of the adhesive.

Example 1. 2,4,6-Tris-14 - carboxylate-phyloxy (2,4,6 -tris-dimetsIminomethyl-1-oxyphenyl) -1, 3,5-triazine (STUP).

To a solution of 10 g (0.02 mol) of 2,4, 6-tris- (4 -carboxyphenoxy) -1,3,5-triazine in 20 ml of dry dimethylformamide with stirring and a solution of 17 g (10 0.06 mol) 2,4,6-tris- (dimethyl aminomethyl) phenol in 20 ml of dry dimethylformamide. The reaction mixture was stirred for 1 h at 3 more hours at. The precipitate formed is filtered off, washed with ethyl acetate (4 x 50 mp) and dried at 50 ° C / 10 mm to a constant weight. 14 g (53%) of PEP are obtained in the form of a slightly yellow amorphous powder with m.p. T74 77 ° С, soluble in water, dasO, N-methylpyrrolidone and ntrobenzape (when heated).

Found: C, 64.82; H, 7.9; N, 12.88.

.one

0

five

0

five

five

0

five

0

Calculated,%: C 64.46, H 7.53, N 13.07.

IR spectrum, 3450 W.S. (OH) 1605 s, (C00), 1570, 1500, 1380 s. (, C N-conp. And cyanurate cycle), 880, 850, 805 s. (deformed .. vibrated. substituted benzene).

PMR spectrum, MD: 7.98 d., 7.22 d. (CgH; ,, J 7.6), 3.58 s. (CH N) 2.22 s. (Nchp.

Example 2. Carried out analogously to example 1, but after adding 2,4,6-tris- (dimethylaminomethyl) -phenol, the reaction mixture was stirred for 0.5 h at which 13.2 g (50%) of STEP was obtained in the form of a slightly yellow amorphous powder. from m.p. 174-177 ° C

Example 3. The procedure was carried out as in Example 1, but after adding 2,4,6-tris (dimethylaminomethyl) phenol, the reaction mixture was stirred. 1.5 hours at, and the precipitate formed is filtered off.

As an epoxy resin, for example, an unmodified epoxydian resin of the ED-20 brand is used. polybutylene glycol duroepoxide or poly vinyl butyral.

The adhesive composition is prepared by mixing the starting components for 10 minutes at 20 ° C. It is a viscous homogeneous mass without visible lumps. When using ED-20 modified polyvinyl butyral epoxy resin, the latter is added to a 10% solution of polyvinyl butyral in a mixture of toluene: ethanol (1: 1), then a hardener is added, mixed and the resulting mass is poured on anti-adhesive paper. After removal of the solvent (10 hours at), an adhesive film is obtained (CHjIaNOf qHs

Ho-o-cHjHjIooc

y /

(C

as a hardener zpoxy resin.

2. A glue composition comprising an epoxy resin and a triazine-containing hardener, characterized in that, in order to increase {CHaljNO-Jt (iHj

HO-O-CHaHjIoDC (CH5) aNCH4 CHj

with the following ratio of components ma.ch.: 40

Epoxydianova

resin100.0

The composition of glue, mac. Epoxy resin grade ED-20

Epoxy resin brand ED-20, modified polybutylene glycol-tanedepoksidom brand PEV-ZAK (30% by weight ZD-20)

, / .--- CH.NtCHj), COONHCH, - (V OH

cHjmcH h

OH

CHtNlCHj)

NIA of viability and bonding strength, 2,4,6-carboxylate-phenoxy- (2,4, 6 -tris-dimethylaminomethyl-1-oxyfenyl) -1,3,5-triazine of the formula used as a triazine hardening agent

CH2N (CHj) 2,

OH

CHjNlCHsb

CHtN (CHsb OH

CUsNlCHj)

The specified triazin-containing hardener

11.5-23.0

100

100

100

100

Epoxy resin brand ED-20, modified polyvinyl butyral brand K (60% by weight of resin ED-20)

Salt 2,4,6-tris- (dimethylaminomethyl) phenol and oleic acid

2,4,6-Tris-4-carbox lat ofenoxy- (2,4, tris-dimethylaminomethyl 1 -oxyphenyl) 11-1,3,5triazine

2-diethylamino-4,6-bis (p-carboxyphenoxy) triazine.

: Properties

Viability at, days

Strength at I shear, MPa, at cure temperature, 3 4s pressure about, 1. MPa,

: 150 ° С, 2h

Note. Shear strength (st, -3) is determined by

  GOST 14759-69 at 20 ° C.

Table continuation

100

15,011,518,7 23,0

120.0 120.0 120.0 120.0

18,027 „0 21.0 30.0

Claims (2)

Formula and Invention 1. 2,4,6-Tris-C4 '-carboxylatophenoxy- (2,4,6-tris-dimethylaminomethyl-1-hydroxyphenyl)] -1,3,5-triazine of the formula _./The ^S -j'CHjNICH,), C00NHCH ₂ -O “OH f \ h _s (chinch, ςΗ ₅ _ nAn_ _CHj , ch ₂ n (ch ₅ ) ₂ Н0 - О-СигН1100С - О-0-ЛИ - - 0 — O“ C06} { HCH ₂ “O“ ^0H (SnlKenG as a hardener of epoxy resin. 2. An adhesive composition comprising an epoxidian resin and a triazine-containing hardener, characterized in that, in order to increase the viability and strength of the bonding ²⁰ , 2,4,6 tris [4-carboxylatophenoxy- (2,4, 6- tris-dimethylaminomethyl-1-hydroxyphenyl) -1,3,5-triazine of the formula iCH ₂ N (CH _s ) ₂ . HE CH _£ N (CH _s h (CHINCH,?, CH _t N (CH _s h ⁿ 0 “О-СН ₂ НЫ00С-О-о0 —О” С00 {шСН _£ -О “0Н (CH _s ) ₂ nAI ^with С ^ H _s ^> CW _t N (CH _s ) _f in the following ratio of components Specified triazinm.h .: 40 containing a hole Epoxydian dyel 11,5-23,0 resin 100.0 Indicators Famous glue Prototype Glue according to the invention ' 1 g I e I 4 The composition of the glue, parts by weight Brand epoxy ED-20 100 100 100 ED-20 grade epoxy modified with poly butyl englycol oluretavdiepoxide grade PEV-ZAK (30% by weight of ED-20) 100 100 14 09630 Table continuation Indicators Izo-Proto ny a type glue Glue according to the invention ED-20 brand epoxy modified with grade K polyvinyl butyral (60% by weight of ED-20 resin) 100 Salt of 2,4,6-tris- (dimethylaminomethyl) phenol and oleic acid 10.0 2,4,6-Tris- [4-carboxylatophenoxy- (2,4,6tris-dimethylaminomethyl-1-hydroxyphenyl)! - 1,3,5triazine 15.0 11.5 18.7 23.0 2-Diethylamino-4,6-bis (p-carboxyphenoxy) triazine Properties Viability at 20 ^ 0, days 1, 0 30 Shear strength, MPa, at a curing temperature of 120 ° C, 3 h, pressure 0.1. MPa 20.7 0.2 120.0. 120.0 120.0 120.0 18.0 27.0 21.0 30,0 150 ° C, 2 h 8.7 Note. Shear strength (st. -3) is determined according to 'GOST 14759-69 at 20 ° C.