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Tetrakisglycoluril derivative and preparation method thereof

A technology of tetramethoxymethyl glycoluril and ethoxymethyl glycoluril, which is applied in the fields of coating, organic chemistry, powder coating, etc., can solve the problems of simple spatial structure and poor stability of polymer molecules, and achieve easy-to-obtain raw materials, Conditions are easy to control and the effect of reducing production costs

Inactive Publication Date: 2015-11-25
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the molecular weight of existing tetramethoxymethyl glycoluril is relatively s

Method used

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  • Tetrakisglycoluril derivative and preparation method thereof
  • Tetrakisglycoluril derivative and preparation method thereof
  • Tetrakisglycoluril derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 3g of tetramethoxymethyl glycoluril, 8g of Amberlyst35 resin, and 60g of PGME into a 250ml three-necked flask, raise the temperature to 60°C, stir and react at -0.08MPa for 9 hours, and distill off the generated methanol at the same time.

[0020] The reactant was suction-filtered with a Buchner funnel, and the filter residue was washed twice with PGME to recover the resin. The filtrate and washing liquid were combined, and the solvent PGME was recovered by distillation under reduced pressure to obtain 5.12 g of 1,3,4,6-tetrakis(1'-methyl-2'-methoxy)ethoxymethyl glycoluril, with a yield of 98.6% .

[0021] Measured product ESI-MS (m / z): 551.2 (M+1).

[0022] IR(KBr)v / cm -1 : 2929, 1712, 1454, 1392, 1110, 1031, 792.

[0023] 1 H-NMR (CDCl 3 ): δ1.02(d, J=6.3Hz, 12H), δ3.112~3.137(q, 4H), δ3.201(d, J=2.23Hz, 8H), δ3.252(s, 12H), δ3.713~3.748 (m, 8H), δ4.548 (s, 2H).

[0024] 13 C-NMR (CDC1 3 ): δ17.1, δ17.1, δ17.1, δ17.1, δ59.6, δ59.6, δ59.6, δ59.6, δ71.2, δ7...

Embodiment 2

[0026] The Amberlyst15 resin was dried in an oven to 60% of its original weight.

[0027] Add 3g of tetramethoxymethyl glycoluril, 6g of dried Amberlyst15 resin, and 70g of PGME into a 250ml three-necked flask, heat up to 60°C, stir and react at -0.07MPa pressure for 17 hours, and distill off the generated methanol at the same time.

[0028] The reactant was suction-filtered with a Buchner funnel, and the filter residue was washed twice with PGME to recover the resin. The filtrate and washing liquid were combined, and the solvent PGME was recovered by distillation under reduced pressure to obtain 5.19 g of 1,3,4,6-tetrakis(1'-methyl-2'-methoxy)ethoxymethyl glycoluril with a yield of 99.8% .

[0029] Measured product ESI-MS (m / z): 551.0 (M+1).

[0030] IR(KBr)v / cm -1 : 2943, 1712, 1485, 1384, 1024, 995, 790.

[0031] 1 H-NMR (CDCl 3 ): δ1.16(d, J=6.3Hz, 12H), δ3.198~3.26(q, 4H), δ3.372(d, J=2.41Hz, 8H), δ3.387(s, 12H), δ3.985~4.032 (m, 8H), δ4.865 (s, 2H).

[0032] 13 ...

Embodiment 3

[0034] Soak the 732 resin in distilled water for 24 hours, then soak it in 2mol / L HCl solution for 24 hours, wash it repeatedly with distilled water until the pH value does not change, filter it and dry it in an oven.

[0035] Add 3g of tetramethoxymethyl glycoluril, 10g of dried 732 resin, and 60g of PGME into a 250ml three-neck flask, heat up to 60°C, stir and react at -0.08MPa pressure for 15 hours, and distill off the generated methanol at the same time.

[0036] The reactant was suction-filtered with a Buchner funnel, and the filter residue was washed twice with PGME to recover the resin. The filtrate and washing liquid were combined, and the solvent PGME was recovered by distillation under reduced pressure to obtain 5.07 g of 1,3,4,6-tetrakis(1'-methyl-2'-methoxy)ethoxymethyl glycoluril, with a yield of 97.8% .

[0037] Measured product ESI-MS (m / z): 551.6 (M+1).

[0038] IR(KBr)v / cm -1 : 2929, 1714, 1479, 1238, 1091, 1031, 790.

[0039] 1 H-NMR (CDCl 3): δ1.14(d, ...

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Abstract

The invention relates to a tetrakisglycoluril derivative. The tetrakisglycoluril derivative has the structural formula (shown in the description). The chemical name is 1, 3, 4, 6-tetrakis(1'-methyl-2'-methoxy) ethoxy methyl glycoluril. The preparation method comprises the following steps: dissolving tetrakisglycoluril in excess propylene glycol monomethyl ether; adding a cation exchange resin catslyst, and reacting under the pressure of 0-minus 0.10 MPa and at the temperature of 40-80 DEG C, so as to obtain the tetrakisglycoluril derivative. According to the tetrakisglycoluril derivative provided by the invention, the branched-chain is extended, the molecular space conformation and density are enlarged, and the crosslinking strength and stability of compounds are improved; as a curing agent for powder coatings, the tetrakisglycoluril derivative can ensure that the powder coatings have better high-temperature resistance and weather resistance, and conditions are created for application of the tetrakisglycoluril derivative to the high-grade, precision and advanced fields like aerospace equipment.

Description

technical field [0001] The invention relates to a curing agent for coatings, in particular to a derivative of tetramethoxymethyl glycoluril and a preparation method of the derivative. Background technique [0002] Tetramethoxymethyl glycoluril is an amino resin curing agent with a wide range of uses and excellent performance. It is developed by Cytel and is mainly used as a curing agent for outdoor powder coatings. Its trade name is Powderlink1174. Tetramethoxymethyl glycoluril can react with polymers containing functional groups such as hydroxyl, carboxyl, amide, carbamate, and mercapto groups to react and crosslink to be cured. At the same time, tetramethoxymethyl glycoluril has a high melting point, which is a Viscous, non-caking, easily crushable solid, therefore particularly suitable for the preparation of durable powder coatings for exterior use. [0003] However, the existing literature reports are all focusing on the synthetic route of tetramethoxymethyl glycoluril,...

Claims

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Application Information

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IPC IPC(8): C07D487/04C09D167/00C09D7/12C09D5/03
CPCC07D487/04C09D5/03C09D7/63C09D167/00C08L91/06C08K5/3445C08K2003/2241
Inventor 赵正保梁瑞张建成刘锐玲卫笑李飞飞
Owner SHANXI MEDICAL UNIV
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