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Acrylamide derivative and preparation method and application thereof

A technology of acrylamide and derivatives, which is applied in the field of acrylamide derivatives and its preparation, can solve problems such as poor corrosion resistance, and achieve the effect of improving sensitivity and increasing sensitivity

Pending Publication Date: 2019-05-31
辽宁靖帆新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In order to solve the problem of poor corrosion resistance of existing acrylic acid copolymers as binders, we propose an acrylamide derivative and its preparation method and use

Method used

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  • Acrylamide derivative and preparation method and application thereof
  • Acrylamide derivative and preparation method and application thereof
  • Acrylamide derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 2-Methyl-N-[4-(phthalimido)phenyl]-2-acrylamide

[0039] Take 21.6g (0.2mol) of p-phenylenediamine and 60g of acetonitrile in a 250ml three-necked flask, stir, heat up to 70°C (oil bath temperature), p-phenylenediamine is completely dissolved, and start to drop 30.8g of methacrylic anhydride (0.2 mol), after 10-15 minutes of dripping, rinse the dropper with 10g of acetonitrile, heat up to 90°C (oil bath temperature), reflux for 6h, remove the oil bath, cool down to 30°C and filter, transfer the filtrate to a 1L three-necked flask, stir, and heat up To 70°C (oil bath temperature), start dropwise adding a solution of 29.6g (0.2mol) phthalic anhydride in 400g acetonitrile, and finish dropping in 2 hours; temperature) reflux reaction for 22h~24h, lowered to room temperature and filtered, washed the filter cake with 2×30ml acetonitrile, and dried the filter cake in an oven at 60°C for 6h to obtain: 38.78g 2-methyl-N-[4-(phthalimide )phenyl]-2-acrylamide, total yield: 63.37%...

Embodiment 2

[0041] 2-[(4-Methacrylamido)-phenyl]-2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid

[0042]Weigh 5.4g (0.05mol) of p-phenylenediamine and 20g of acetonitrile in a 250ml three-neck flask, stir, heat up to 70°C (oil bath temperature), p-phenylenediamine is completely dissolved, and start to drop 7.7g of methacrylic anhydride ( 0.05mol), after 10-15 minutes of dripping, rinse the dropper with 5g of acetonitrile, heat up to 90°C (oil bath temperature), reflux for 6h, remove the oil bath, cool down to 30°C and filter, transfer the filtrate to a 500ml reaction bottle, stir, Raise the temperature to 70°C (oil bath temperature), start to add 3.7g (0.025mol) triethyl orthoformate + 10g acetonitrile dropwise, and finish dropping in 10 minutes; then start to dropwise add 9.6g (0.05mol) trimellitic anhydride + 125g acetonitrile solution, drop in 2 hours Complete; during the dropping process, solids were continuously precipitated. After the dropping was completed, the temperature wa...

Embodiment 3

[0044] N-(2-Hydroxy-4-nitrophenyl)phthalimide

[0045] Weigh 11.6g (0.075mol) of 2-amino-5-nitrophenol and 113ml of glacial acetic acid into a 500ml four-neck flask, add 22.3g (0.15mol) of phthalic anhydride, heat up to 128°C and reflux for 3 hours, remove the oil bath, and To room temperature, add 50ml of pure water, stir for 10min and then filter, wash the filter cake with 2×50ml of pure water, then transfer the solid + 232ml of pure water to a 500ml four-neck flask, stir for 30min, filter, and dry at 60°C for 10h to obtain: 20.15 g, purity: 99.11%, yield 94.6%. 1H-NMR (DMSO) δ11.02 (1H, s, OH), 8.01~7.99 (2H, q, Ar-4, 7H), 7.94~7.93 (2H, q, Ar-5', 6'H), 7.82-7.79 (2H, m, Ar-5, 6H), 7.64-7.63 (1H, d, Ar-3'H).

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Abstract

The invention provides an acrylamide derivative and a preparation method and application thereof. The acrylamide derivative is represented by general formula shown in the description, wherein R is oneof-H,-OH or-COOH, and R1 is one of-H,2-OH or 3-OH.The acrylamide derivative has the beneficial effects that the phthalimide substituted acrylamide derivative is used as a comonomer of an acrylic copolymer andprevents the corrosion resistance of the acrylic copolymer to chemicalprints; meanwhile the acrylamide derivative improves the sensitivity, the wear resistance and the development adaptability of a lithographic plate material.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to an acrylamide derivative and its preparation method and application. Background technique [0002] The structural formula of acrylic acid is: its α-position and β-position hydrogen can be substituted; its carboxyl group can be derived from ester group (including diester, polyester), amide, acid chloride, acid anhydride, etc.; nitrile can also be broadly regarded as carboxyl group derivative. Therefore, many of its derivatives can be polymerized, and it is an important class of ethylenic monomers. [0003] Polyacrylic acid monomer is acrylic acid, which is mainly produced by catalytic oxidation of propylene or acrolein in industry. It is a liquid with a melting point of 12°C and a boiling point of 142°C. It has a pungent smell similar to acetic acid. Generally, the polymerization is carried out in an aqueous solution state. Its polymerization rate in water is greatly affected ...

Claims

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Application Information

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IPC IPC(8): C07D209/48C08F220/60G03F7/039
Inventor 刘扬杜富强
Owner 辽宁靖帆新材料有限公司
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