SU767104A1 - Diglycidylic acetal-containing ethers of aromatic diols as binders for preparing polymeric mastics,hermetics and coatings and their preparation method - Google Patents

Description

R. is lower alkyl; --CMiWHCOiCHtl -) o-. n - 1-3. . / “Diglycidyl ethers of formula 1 are obtained by reacting bis- or diphenol with vinyl glycidyl ether of formula CHjsiCHo (CHiCHjo) n CHj, - CH - dHi / d where n has the indicated value, at a temperature of 20-50 s in the presence of organic perfluoride acid in the - quality talisa lera SNg-O-CHj-CHj-o in a flask equipped with a stirrer and a thermometer, was charged with 22.8 g of diphenylolpropane and 31.8 g of vinylglyl cidyl ether of ethylene glycol. At 20 ° C, 0.09 g of CFjCOOH is introduced. The reaction temperature rises by self-heating up to. The process of interaction takes 10 minutes, after Che. fo in-water t 0.09 ml of triethylamine. The resulting acetal-containing glidine ester has the characteristics shown in Table. 1. l l: l T a b l and c a

Content, 1

C62.3 62.9

. And 7.4 7.8

The content of the epoch; ..

The main groups,% 16.0 17.4

  CK, -ca -cKt-o-cHi-cKi-o-cK-o / 1

about -; CHj

 A flask equipped with a stirrer and a thermometer was charged with 21.8 g of vinyl glycol Dylether Etylene Glycol and 10.2 g of a mixture of alkyl resorcinol containing 23% of OH groups was dissolved in it. When OG is introduced, 15GCS7CUN. The temperature rises to 64 s. Process B (travels 40 min at, ps5 after which 0.1 pml of triethyl is introduced,

The resulting acetal-containing glycidyl ether has the characteristics shown in table. 2

 b. l and c

57.2

56.9 8.0 8.4

k18 L 20%

OU temperature

-72

P p. Of measure 2. Preparation of 1,3-bismethyl 1-cetbetseigl cidyl-5-ethylbenzene of the formula.

o-ot-o-eMj-CHi-o-Cttj-CH-CH, 1 /

CjHs CHjo

 Continued table. 2

0 Sodeckiye vyyyl0, 00. jftjx groups,%

Content hydro0, 12

L strong groups,% 362

Molecular weight

Viscosity at

11; 25 ° C, P

31.5

Product yield, g Product yield, 99

Glass transition temperature 5 ° C

 75 The yield of the desired product is up to 98%. The proposed method is carried out for 3-40 minutes depending on the bisphenol and the catalyst used. At the end of the process; the catalyst is neutralized with a tertiary amine. The process according to this method can be conducted periodically; as well as in continuous installations. The preparation of such compounds under the conditions of the proposed method was not known. Example. The preparation of 4,4-bis-methyl acetal ethoxyglycyl diphenyl propane of the formula -.,. V O-CH-U-Cttj-CHj-O-CHj-OT-CH, shlV Continued table. Yd51od product, g54 Product yield,% 98 Viscosity at 25 ° С, П80

btt-CH -cHjo {eHt) tOCOKKCH: j- / VcHj, imcoe (arj) iOPHtCR 5i,,

00

in a flask equipped with a stirrer and a thermometer, when a gram of glycol carbonate is dissolved in 43.8 g of diethylene glycol vinylglycidyl ether, the mixture is cooled to 50 ° C and 0.2 g of C F-jCOOH is added. The temperature of the mixture rises to 90 ° C. Process;

10 min. without heating, 0.2 ml is introduced into the reaction mixture after QB

triethylamine.

The resulting acetal-containing glycol-1-carbrnate target, the product has the characteristics shown in table. five.

Table 5

Continuation of the table. 6

52 7.7

51.7 7.2

4.1 4.7

11.5

10.9

0.00 0.00

0.07

0,0,0 674

675 76.5 98

Viscosity at

and

Tamper Atura. Glass.

Example 6. Preparation of 4,4-bismethyl-Cetal-Diethoxy-glycidyl-diphenyl-propane of formula t, in which B a, p 2.:. ../. -.-: H -; :: -: -:

In a flask equipped with a stirrer and thermometer load 22.8 g of diphenylolpropane and 4I, 4 g of vinylglycerol ether diethylene gdacol. When 0.11 g is administered. The reaction temperature spontaneously rises to .. The process is carried out for: 10 minutes, after which, 0.11 PP of triethylgly is introduced. ; ..: ... ..: -.,; - ..; -;: - .v-,.

Exit 64 g .. l.

The resulting 4,4-bis-me1 acetylg-) diethoxyglycidyl diphenylpropane has the characteristics shown in

tab. 6. -. . -: -: .-

. ----- g 7. Preparation of 4,4-bis-methyl acetal triexylglycidyl diphenylpropane,

. Similarly to the conditions of example 1, smyshvayt 22.8 g of diphenylpropane, 53.3 g of vinyl glycidyl ether of triethylene glycol and 0.15 g. The process is carried out for 20 minutes, after which 0.15 ml of triethylamine is introduced.

Exit 76

The obtained 4,47 bis-methyl acetal triethoxy glycidyl diphenyl propane has the characteristics shown in table. 7

Table 7

Content%

. WITH

50.1

50.6. .n: 7.9 7.6

Content of epoxy, groups,%

11.7 12.5

Content of vinylideIS groups,%

0.00 0.00

0.15 0.00

557

570

Yusts prokalny resins ED-20 and EIS-1 and the proposed esters (resin ED-B-15.5 - compound of formula 1, where R a, resin EIS-B-22,3 - compound of formula I, where R b with R - CHS, as a filler marshalite - 140 weight, h, as a hardener - xylylenediamine, in a stoichiometric ratio.

Strength at stretching, MPa 20.6

Relative elongation at break,%, 0.39

Internal stresses at

hardening on a concrete substrate, MPa 3.9

Abrasive jet wear

see mi n0,46

Water absorption in 24 hours,% 0.30

Specific impact viscosity

Kpa / m4,1

P. r. And m. N and. MPa - definition by Pascal method. Data on the impact resistance of compositions based on known binders with the introduction of the proposed (ED-B-15.5 resin and EIS-B-22.3 resin) and compositions based on known epoxy oligomers without the addition of those proposed are presented in Table. 9. As a hardener, xylylenediamine was taken in stoichiometric ratio. The curing mode of the compositions is similar to that indicated: delaying 30 days, at 20 + 2s. Composition 1, parts: Resin ED-20 Marshalite

Samples were made in a paddle mixer for 12 minutes at and contained for 30 days at.

Comparative data on the elasticity of polymer compositions based on the proposed and known binders are presented in Table. eight,

Table 8

29.8

26.7

18.2

19.8

19.3

0.34

4.1

0.45

0.35 3.9

0.27

0.22

0.51

0.35

C, 35

0.25

18.3

18,8

3.7 Composition 2, parts by weight. 5 Resin ED-20 Resin ED-B-15.5 Marshalite Specific impact viscosity of components 1–3, 9, composition 2 - 11.4 KPa / m. Composition 3, parts by weight: Resin EIS-1 100 Marshallite 140 Composition 4, parts by weight: Resin EIS-160 Resin EIS-B-223-40 Marshallite 140

The specific impact viscosity of the composition is 3–3.7, composition 4–16.3 KPa / m.

thus, with the veedemimas of the proposed esters of formula 1, there is a moiety CHi-CK-CHi- (oCHj, CH;,) n-o-cH-o-R-o-CH. . f (ff (3 is lower alkyl. x -CHi-KHCo (CHj) 4; O p is an integer of 1-3, as a binder for the preparation of polymeric mastic sealants and coatings. 2. A method for the preparation of diglycidyl acetal esters of aromatic diols by PL, I differ by the fact that bisphenol or diphenol is reacted with vinylglycidyl ether of formula CH3, CHO (CKiCHtO) nCHi-CH-CHt: O.

This is an increase in the impact resistance of the compositions.

Claims (1)

Claim 1. Diglycilyl acetal-containing esters of aromatic diols of the general formula / V. {x (cHj-CH: io) n-CHi-cH-; Hj gdg p- has the indicated value, at a temperature of 20-50 C in the presence of organic perfluoroacid as catalyst, followed by separation of the target product. Sources of information taken into account during the examination 1.. Blagonravova A.A. et al. Varnishes. epoxy resins, m., Himi, 1U / 0, p. 60. 2. US patent No. 2585115, cl. 260-47.1, publ. 1945.