Quaternary trimethylammonium salt of 1,3,5-triazine as an intermediate product in the synthesis of modifier - souvenires of epoxyalkanes in the anhydrous compositions curing

 

(57) Abstract:

The invention relates to organic chemistry, in particular Quaternary ammonium salt of 1,3,5-triazine of the formula (1) as an intermediate product in the synthesis of modifier-souvenires of epoxyalkanes to improve technology use, increase heat and heat resistance, specific toughness, hardness Barkely, compressive strength and output of the gel hardened epoxy composites, as well as to reduce the time of gelation, water absorption and temperature combination epoxy compositions. table 2.

The invention relates to the field of organic chemistry, specifically to the new derived SIM-triazine: 2-ammonium-chloride-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (TAHT) formula:

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which is the active floor product synthesis (synthon) modifier-souvenires epoxy oligomers 2-allylamino-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine of the formula:

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Known trimethylammonium salt derivatives SIM-triazine containing alkylamino substituents in positions 4,6-triazine cycle, such as N(CH3)2and N(C2H5)2, coalisland derivatives SIM-triazine [see Century Century Dovlatyan, K. A., Eliasen, A. C. Dovlatyan. Rearrangements in the row halogenoalkane (amino)-s-triazines. - CHC. 1977, 7, S. 989-992] . The use of such salts as synthons in the synthesis of modifiers-sommerdale epoxy oligomers is unknown.

Also known 2-diethylamino-4,6-bis[ethoxycarbonyl(4'-phenoxy)]-sym-triazine (DECT) and its use as a modifier of epoxy compositions anhydrite curing. Get DECT reaction of the acid chloride of 2-diethylamino-4,6-bis(p-carboxyphenoxy)-SIM-triazine with absolute ethyl alcohol in solution in benzene, in the presence of triethylamine, as an acceptor of hydrogen chloride, when equimolar the ratio of the source. Introduction DUCT in the composition in an amount of 10 wt.% when 90oWith allows you to get cured composites with thermal stability in air 285oWith heat Vika - 110oWith, the specific impact strength of 4.5 kJ/m2with a compressive strength of 100 MPa and hardness Barkely 28 barque, absorption of 0.12 wt.% and the output of the gel - 93,8 wt.% [see C. K. Pyzhov, C. N. Zaplishny, A. A. Balian, G. M. Poghosyan. Synthesis of some esters and amides of 2-substituted 4,6-bis(p-carboxyphenoxy)-s-triazines. LTS, 1981, 10, S. 1406-1411 and E. A. Hakobyan, V. K. Pyzhov, C. N. Zaplishny,s, 1983, 10, S. 57]. Nedostatkami application DECT is a high temperature combining it with epoxy oligomer (90o(C) that affects the manufacturability of the use, inability to act as a modifier-souvenires (as evidenced by the low efficiency of gelation and relatively high water absorption), as well as lack of effectiveness increase heat and heat resistance, specific toughness, hardness Barkely and compressive strength of hardened composites (similar in structure and application).

Technical solution to the problem is the improvement of the efficiency of use, increase heat and heat resistance, specific toughness, hardness Barkely, compressive strength and output of the gel hardened epoxy composites, as well as reducing the time of gelation, water absorption and temperature combination of epoxy compositions anhydrite curing.

The task is achieved by the fact that the newly synthesized 2-trimethyl-ammoniacal-4,6-bis(ethoxycarbonylmethylene)-1,3.5-triazine (TAHT) formula:

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use as an intermediate compound for the synthesis of effective modifier-souvenires epoxy compazine 2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)-1,3.5-triazine as an active Cinchona allows to synthesize effective modifier-coommercial of epoxyalkanes and get anhydrite curing composites, different elevated heat and heat resistance, specific toughness, hardness Barkely, compressive strength and higher yield of the gel hardened epoxy composites, and low gelation time, water absorption and temperature combined with epoxy resin.

When cyanuric chloride - technical product was then purified twice by crystallization from carbon tetrachloride (so pl. 146oC). Ethyl ester aminouksusnoy acid get by a known method Fisher interaction hydrochloride aminouksusnoy acid with an excess of ethyl alcohol and subsequent dehydrochlorination using dry ammonia [see E. Fisher. Ber., 1901, Bd. 34, p. 433] . The triethylamine before use, dried over sodium hydroxide and distilled with an efficient reflux condenser (so Kip. 89-90oC). Similar in structure and application of DECT get by a known method by the interaction of the acid chloride of 2-diethylamino-4,6-bis(4'-carboxyphenoxy)-SIM-triazine with ethanol in the presence of triethylamine acceptor - hydrogen chloride [see C. K. Pyzhov, C. N. Zaplishny, A. A. Balian, G. M. Poghosyan. Synthesis of some esters and amides of 2-substituted 4,6-bis(p-carboxyphenoxy)-s-triazines. CHC, 1981, 10, S. 1406-1411].

In the synthesis of modifier-souvenires of epoxyalkanes presented below.

Example 1. 2-Trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (TAHT). To a solution of 4.62 g (24 mmol) of 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) in 20 ml of absolute benzene at a temperature of 51oC and stirring slowly added dropwise a mixture of 5 g (48 mmol) of ethyl ether aminouksusnoy acid (ethyl ester of glycine) and 4,96 g (49 mmol) of fresh of triethylamine in 5 ml of abs. benzene and continue stirring 1 h at the same temperature, 1 h at 25-30oC and 1 h at 35-40oC. the precipitation is filtered off, the filtrate is evaporated to dryness in a water-jet pump vacuum and the dry residue was washed with water (350 ml) and dried. Get 6,1 g (71%) of 2-chloro-4,6-bis(ethoxycarbonyl-letmetellyou)-1,3,5-triazine (HAT) in the form of a white crystalline powder with so pl. 178-179oC.

Found, %: C 41,71; N 5,19; N 22,18; Cl 12,05; C11H16N5ClO4.

Calculated, %: C 41,58; N 5,08; N 22,04; Cl Of 11.15.

X , cm-1: 3250, 3180cf.(N-H); 1740S.(C=O); 1575, 1540,c.cp.,(C=C and C=N-comp.); 1240cp.(C-N); 1190 ,1130cf(C-O-C).

PMR-spectrum , M. D.: 8,10ush.with.(2H, -N-H); 4,05...4,20m. (4H, -CO2); 3,85...4,0m(4H, -NCH2); 1,20... 1,30m(6N, -CH3).

Mol. ion 317 (Ivanyi and a temperature of 101oWith in a stream of nitrogen is bubbled dry trimethylamine. The saturation of trimethylamine continued for 1 h and the reaction mixture is stored at 20oWith 12 o'clock Formed abundant precipitate is filtered off, washed with abs. benzene (325 ml) and dried in vacuumassisted to constant weight. Get of 5.81 g (98%) 2-trimethylammoniumchloride-4,6-bis (ethoxycarbonylmethylene)-1,3.5-triazine (TAHT) in the form of a white crystalline powder with so pl. 180-180,5oC.

Found, %: C 44,73; N For 6.81; N 22,40; Cl At 9.53. WITH14H25N6lO4.

Calculated, %: C 44,59; N 6,69; N 22,30; Cl 9,40.

X , cm-1: 3435, 3225cf. (N-H); 1730with. (C=O); 1590, 1560, 1510S.,cf.(C=C and C=N-comp.); 1190, 1150cf.(C-O-C).

PMR-spectrum , M. D. : 8,12ush.with(2H, N-H); 4,08... 4,23m. (4H, OCH2); a 3.87...4,01m(4H, NCH2); 3,20m(N, N(CH3)3); 1,22...1,31m(6N, -CH3).

Example 2. Carried out under conditions analogous to example 1, from 5 g (16 mmol) HAT in 35 ml of abs. benzene, with the only difference that the bubbling dry trimethylamine continue for 1.5 h at 51oC, then incubated the reaction mixture at the 18oWith another 15 hours and get by 5.87 g (99%) 2-trimethylammoniumchloride-4,6-bis(taxicab the ptx2">

Found %: 44,73; N For 6.81; N 22,40; Cl At 9.53. C14H25N6ClO4.

Calculated, %: C 44,59; N 6,69; N 22,30; Cl 9,40.

X , cm-1: 3435, 3225cf.(N-H); 1730S.(CO); 1590, 1560, 1510with,cf.(C=C and C=N-comp.); l190, 1150cp.(C-O-C).

PMR-spectrum , M. D. : 8,12ush.with.(2H, N-H); 4,08...4,23m(4H, OCH2); a 3.87...4,01m(4H, NCH2); 3,20m(N, N(CH3)3); 1,22...1,31m(6N, -CH3).

The obtained Quaternary ammonium truthinamerica salt TAHT is an effective intermediate (synthon), suitable for the synthesis of more active, in comparison with known modifier-souvenires epoxy oligomers. Examples of obtaining modifier-souvenires on the basis of the proposed Sinton presented below.

Example 3. 2 Allylamino-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (AECT). To a solution of 5 g (13 mmol) of 2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)-1,3.5-triazine (TAHT) in 35 ml of acetonitrile, with stirring, and the temperature 51oWith slowly added a solution of the mixture of fresh and dried 0.75 g (13 mmol) of allylamine and of 1.32 g (13 mmol) of triethylamine in 5 ml of acetonitrile. The mixture is stirred for another 1 h at the same temperature is fallen precipitate is filtered off, washed with water (425 ml) and dried. Gain of 3.3 g (73%) 2-allylamino-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (AECT) in the form of a white crystalline powder with so pl. 78-79oC.

Found, %: C 49,81; N 6,69; N 24,93. WITH14H22N6O4. Calculated, %: C 49,69; N 6,55; N To 24.84.

X , cm-1: 3330, 3220cf.(N-H); 1710S.(C=O); 1640cf.(C=C); 1600SL., 1565S.(C=C and C=N-comp.); 1180, 1140cf.(C-O-C).

PMR-spectrum , MD.: 6,70ush.with.(3H, NH); 5,75...5,90m(1H, CH); 4,95... 5,15D. D. D.(2H, CH2SN= J=17, 42 and 13); 4,0...4,15m. (4H, NH); 3,75...4.0 m (6N, ); 1,15...1,30m(6N, CH3).

Mol. ion 338 (mass by a spectroscope).

Example 4. Carried out under conditions analogous to example 3, from 5 g (13 mmol) of 2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (TAHT) in 35 ml of acetonitrile and a mixture of 0.75 g (13 mmol) of allylamine and of 1.32 g (13 mmol) of triethylamine in 5 ml of acetonitrile, with the only difference that the addition of a mixture of amines is carried out at 101oC, and the stirring of the reaction mixture, a further 1.5 h at this temperature and 10 h at 201oWith and obtain 3.6 g (79,6%) 2 allylamino-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (AECT) in the form of a white makakasali is chileno, %: 49,69; N 6,55; N TO 24.84.

X , cm-1: 3330, 3220cp.(N-H); 1710S.(C=O); 1640cf.(C=C); bCL., 1565c.(C=C and C=N-comp.); 1180, 1140cf.(C-O-C).

PMR-spectrum , M. D.: 6,70ush.with.(3H, NH); 5,75...5,90m. (1H, CH); 4,95... 5,15D. D. d. (2H, CH2(CH) J=17, 42 and 13); 4,0...4,15m(4H, NH); 3,75...4,0m(6N, ); 1,15...1,30m(6H, CH3).

Mol. ion 338 (mass by a spectroscope).

Specific examples of the use of AECT obtained on the basis of the proposed intermediate, as a modifier-souvenires of epoxyalkanes to increase heat and heat resistance, specific toughness, hardness Barkely, compressive strength and output of the gel hardened epoxy composites, as well as reduce the time of gelation, water absorption and temperature combination are presented in tables 1, 2 (examples 5-11; see the end of the description).

The original epoxy composition is prepared on the basis of epoxyalkanes ED-20, svejeprigotovlennogo from CCl4phthalic anhydride, a known modifier of DECT and obtained on the basis of the proposed intermediate - modifier-souvenires AECT, in exact accordance with the known method [see E. A. Hakobyan, V. K. Pyzhov, C. N - Layer. mass, 1983, 10, S. 57]. Modes of curing epoxy compositions similar to the same method. The output of the gel is determined by boiling the sample of the cured composite in acetone, to conventional Soxhlet extractions within 12 hours of the Time of gelation and water absorption is determined in accordance with a known method [see L. S. Kalinin, M. A. Motorina, N. And. Nikitin and other Analysis of the condensation polymers. M.: Chemistry. 1984. - 296 S.].

As can be seen from table 1, the application of the proposed modifier-souvenires EECT in comparison with known DECT allows to reduce the temperature of its alignment with epoxyalkanes at 37o(53 instead of the 90o(C) that simplifies the technology of preparation of original compositions.

From the same table shows that the use of AECT part epoxy composition allows to reduce the gelation time at 65, 75 and 95oTo 47-124 min, 34-90 min and 7-32 min, respectively, instead 2500-760 min in the case of control and 1300-380 min in case of using a known modifier of DECT, which suggests that the proposed EECT, unlike known DECT, is both effective sommerdale epoxy compositions anhydrite curing.

The effectiveness of AECT as souveni the th output of the gel in utverzhdenii composition in comparison with control 8.6 and 11.8%, at that time, as a known modifier of DECT increases this rate by only 7.8% (94,6-97,2% instead 86,0%).

From table 2, examples 5-11 also shows that the proposed EECT is more effective modifier epoxyalkanes in comparison with the famous.

So, using EECT allows to obtain a cured epoxy composition, the heat Vika and temperature resistance which 44-57 and 60-75oWith respectively exceeds that in comparison with the control, while using a known modifier of DECT allows you to increase these figures only 39 and 50oRespectively (115-128oAnd 295-310oWith, respectively, compared to 71oC and 235oC, respectively).

Specific impact strength of the composition, utverzhdenii using AACT, increased by 0.8 to 2.6 kJ/m2in comparison with the control, while using a known modifier of DECT increases this rate of 0.5 kJ/m2(4,8-6,6 kJ/m2instead of 4.0 kJ/m2).

The compressive strength of the composition, utverzhdenii using AACT, increased by 28-48 MPa in comparison with the control, while using famous DECT, the confirmed using AECT increases on 4-15 bark in comparison with the control, while using famous DECT increases this rate by only 3 bark (29-40 bark instead of 25 bark).

Water absorption of the composition, utverzhdenii using AECT reduced by 30-70,9% in comparison with the control, while using famous DECK at this rate, the impact may have little (or 0.035-0,084 wt.% instead of 0.12 wt.%).

Thus, the application of the proposed Quaternary ammonium salt of 1.3.5-triazine as an intermediate in the synthesis of modifier-souvenires allows you to get the modifier-coommercial, which is used in the composition of the epoxy compositions provides, in comparison with known lower temperature combination that improves workability and hardened composites reduces water absorption and increases the output of the gel increases heat resistance, thermal stability, specific impact strength, hardness and compressive strength.

Quaternary trimethylammonium salt of 1,3,5-triazine of the formula

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as an intermediate product in the synthesis of modifier-souvenires of epoxyalkanes in the anhydrous compositions of curing.

 

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15 cl, 2 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to hydroxyphenyltriazine UV-radiation absorbents for protecting transparent plastic containers or films and their contents. Description is given of oligoester or polyester with general formula -[A-O-D-O]x- as an additive to thermoplastic polymer material, where x - ranges from 1 to 50; A - is a hydroxytriphenyltriazine residue with formula (II) or assumes one of the values, indicated for T; D - C4-C12alkylene, which can be substituted with OH, and/or include O; L - C1-C18alkylene; C5-C12cycloalkylene; C3-C18 alkenylene, which can be substituted with phenyl, C7-C11alkylphenyl, C5-C12cycloalkyl, OH, halogen, C1-C18alkoxy group, C5-C12cyclolkoxy group, C3-C18alkenyloxy group, COOH; R1 - H, OR7 or OH under the condition that, at least one of R1 or R13 represents OH; R7 - hydrogen, C1-C12alkyl or L-CO-O-R9, where R9 - H, C1-C18alkyl, C2-C12hydroxyalkyl; R10 - hydrogen, C1-C4alkyl, Cl, phenyl or -OR7; R11 - hydrogen, methyl; R13 - hydrogen, methyl, OH, OR7; and T - is a bivalent acyl residue of aliphatic or cycloaliphatic C13-C60 dicarboxylic acid, and which includes at least one fragment with formula (II) and at least one fragment T.

EFFECT: effective protection of products in thin-walled containers or films.

13 cl, 8 ex

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