SU753847A1 - Tris-2,4,6-(3'-phenoxy-2'-oxypropyl-1'-oxy)-methylisocyanurate as adhesion additives to glue-melts - Google Patents

Description

The invention relates to a new derivative of isocyanuric acid, which increases the adhesion of hot melt adhesives, which can be used in the manufacture of adhesives. It is known to use as an adhesive additive to glue m-melts of rosin ij. The disadvantage of this known means is that the hot melt adhesives obtained with its use do not provide high bonding strength, require a long time of hardening and are characterized by a high melting point. In structure and the effect achieved, the three (- methylglycidyl) are closest to the proposed compound. -. -isocyanurate, used as an aft-additive G2 j. The disadvantages of this known derivative of isocyanuric acid are the low bonding strength of hot melt adhesives obtained using this agent, the long time to set and the high melting point of these adhesives. The purpose of the invention is to obtain new cyanuric acid derivatives, which provide higher bonding strength, reduced setting time and melting temperature of melt glue. Tris-2,4,6- (3-phenox-2-oxypropyl-1-ox1 methylisocyanurate of the formula

OHjC-Ctt-OHj-OHj4n / L

s-1G -sn,

2v-v 2 K C H20-OH

CHj-dH-tJHaO

Sn, oV as an adhesive additive to glue m -. alloys. The method of preparing the compound according to the invention is based on the known reaction of opening oxiranes with alcohols in the presence of a base and involves the reaction of a trismethylol isocyanuric acid derivative with a phenylglycidyl ester. Below are examples of the preparation of Tris-2,4,6- (3-phenoxy-2-oxypropyl-1-oxymethyl isocyanurate. Example: 8.2 g (0.038 mol) of trimethylolisocyanurate, 20, are loaded into a three-necked flask equipped with a mechanical stirrer , 7 ml (0.152 mol) of phenylglycidyl ether and 1 ml of dimethylaniline. With vigorous stirring, the temperature of the reaction medium is raised to and maintained at this temperature for 3.5 hours, and then at 1OO ° C for 3.5 hours, the reaction is completed, the highly viscous resin is mixed in ethyl alcohol (the target product is not after treatment with ethyl alcohol and drying in vacuo a white crystalline substance is isolated. The yield is 75%; mp 85 ° C, Found: C 59.19; H 5.79; N6 , 27. Vyiseno.%: C 59.07; H 5.70; C6.19; Example 2: 8.2 g (0.038 mol) of trimethylolysocyanurate, loaded with a mechanical stirrer, are charged with a three-neck flask, 20.7 ml (0.152 mol) of phenylglycidyl ether and 1 ml of dimethyl aniline. With vigorous stirring, the temperature of the reaction medium is raised to 9 ° C and maintained at this temperature for 3 hours, and then at 105 ° C for 3 hours. Upon completion of the reaction, the resulting high viscous resin is stirred in ethyl alcohol and the target product is separated by filtration. After treatment with ethyl alcohol and drying in vacuo, a white crystalline solid is isolated. Product yield 80%; m.p. 85 C. Found,%: C 59.19; H 5.79; N6,27. Calculated,%: C 59.07 H 5.70; N6.19. The molecular weight of Tris-2,4,6- (3-phenoxy-2-hydroxypropyl-1-hydroxy) -methyl-isocyanurate is determined by cryoscopy. Found: mol.ves. 650. Vyisleno: mol. 653. In the IR spectra, absorption bands were observed in the regions of 763 cm (isocyanuric ring), 1150 cm (aliphatic ether group), 1250 cm, 1O55 cm (aromatic ether group), 142 Ocm. 130O (secondary alcohol). Others according to the test of the proposed compound as an adhesive additive in adhesive compositions in comparison with the known means of similar purpose are given in the table.

Known adhesives Polyamide

Rosin Carnauba Wax

Polyamide

Rosin (adhesive additive)

Carnauba wax Trimethoxyglycidyl isocyanurate (TMGIC) (adhesive additive)

150

20

5.6

14O

sixteen

9.5

.Polyamide

Rosin Carnauba Wax

Tr i- (v-met ilgl ici dil) -isocyanurate (adhesive additive)

Adhesives with the addition of Tris-2,4,6- {3-phenoxy-2-oxypropyl 1-oxy) -methyl isocyanurate

.Polyamide Carnauba wax

Tris-2,4,6- (3 phenox-2-hydroxypropyl-1-oxy) -methyl isocyanurate

.Polyamide Rosin Karnaubsky wax

Tris-2,4,6- (3-phenoxy-2oxypropyl-1 -oxy) -methyl isocyanurate

Known adhesives

.Polyamide

Ethylene copolymer

Styrene termoelastoplasg

Agent stickiness Plasticizer Polyether TF-82

.Polyamide

Ethylene copolymer with vinyl acetate

Butadiene styrene thermoplastic elastomer

Agent stickiness Plasticizer Pckpief TF-82 TMGIC Polyamide

Ethylene copolymer with vinyl acetate

Table continuation

7.2

14O

17

10.3

140

sixteen

14O

12.5

sixteen

120

15

115

25

Tr io. (methylglycylation) aocyanurate

Adhesives with. Tris-2,4,6- - (3-phenoxy-2-oxnprshil-1-oxn) -methyl-eocyanuraga additive

Polyamide

Ethylene copolymer

tatom

Butadiene styrene thermoelas-,

toplast

Plasticizer Polyether TF-82.

Tris-2,4,6- (z -phenox 2-oxypropyl-oxy) methyl-Zo. CyanuratePolyamide

,

Ethylene copolymer with vinyl acetate

Butadiene styrene thermoplastic elastomer

Agent stickiness Plasticizer

Polyester TF-82

Tris-2,4,6- (3-phenoxy-2-hydroxypropyl-1-oxy) -methyl isocyanurate

Known adhesives Polyethylene Rosin Polyisobutylene Alumina Polyvgiloyl alcohol Polyethylene wax Polyethylene Rosin Polyisobutylene

753847

8 Continuation of the table

/ 5.2

6.4

115

ZO, 5

2.8 6.7 3.7

9.3 5.2

4.6

4.6

11S

.34.4 64.4 15.5

3.7

2.0

32.5 32 21.8

140

20.5. 21.8 2.0 8.8 35.0 26.2 18.0

9

Tr is- {ft-met ilglycidyl) - isocyanurag6,5

Adhesives with the addition of TRIS-2, 4,6- {3-phenoxy-2-oxypropyl-1-oxn) methysocyanurate

f Polyethylene41,3

Polyisobutylene31,1

Alumina oxide 4.4

Polyvinyl alcohol4,2

Polyvinyl Wax9.9

Tris-2,4,6- (3-phenoxy-2-hydroxypropyl-1-oxy) -methyl isocyanurate-9, 1

.Polyethylene2O, 9

Rosin .32,0

Aluminum oxide 2.0

Polyvinyl alcohol-1,5

Polyethylene wax7,3

Tris-2,4,6- (3 -phenoxy-2-oxypropyl-1-oxy) -methyl isocyanurate .5.1 The recipe for glue 3 is a comparative example (not described in literature). As can be seen from the table, the introduction of Tris-2,4,6- (3-phenoxy-2-oxypropyl-1-oxy) -methyl isocyanurate to the compositions of the adhesives improves their physical and mechanical properties (increases the bonding strength, reduces the setting time and

7 53847

ten

Continued tablegats

13O

32.1

13O

Claims (1)

35.0 reduces softening temperature) compared with the known adhesives and additives. Tris-2,4,6- (3-phenoxy-2-hydroxypropyl-1-hydroxy) -methyl isocyanurate formula