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Photo-curing monomer with ortho-phenolic hydroxyl structure, preparation method and bond thereof

A technology of o-phenolic hydroxyl and light curing, which is applied in the direction of non-polymer organic compound adhesives, cyanide reaction preparation, chemical instruments and methods, etc., to achieve the effects of wide practicability, low preparation cost, and easy operation

Inactive Publication Date: 2013-08-14
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main purpose of the present invention is to solve the common problem that the currently commercialized adhesives cannot have fast and long-lasting adhesion in both dry and wet states, and obtain fast and long-lasting adhesion that can bond both in dry and wet states. agent

Method used

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  • Photo-curing monomer with ortho-phenolic hydroxyl structure, preparation method and bond thereof
  • Photo-curing monomer with ortho-phenolic hydroxyl structure, preparation method and bond thereof
  • Photo-curing monomer with ortho-phenolic hydroxyl structure, preparation method and bond thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] Dissolve 10 g of dopamine hydrochloride in a mixed solution of 200 ml deionized water and 40 ml ethanol, fill with nitrogen for 20 min, then add 19.8 g of acryloyloxyethyl methacrylate, and 6 g of triethylamine, at 35 The reaction was carried out at ℃ for 6 hours until the solution was clear. The reaction solution was extracted with a mixed solution of 160ml of ethyl acetate and 40ml of ethanol, and then the ethyl acetate layer was evaporated to remove the solvent with a rotary evaporator to obtain 18.6g of the product. NMR 1 H-NMR identification, 1 H-NMR (DMSO, 600MHz): δ (ppm): 1.93 (CH 3 ); 2.35, 2.65, 2.69, 2.75, 4.36, 4.43 (CH 2 ); 6.42, 6.51 (CH, Ar); 5.58, 6.15 (=CH 2 )

[0043]The product is diluted with acetone to form a solution with a weight percentage of 75%, adding 2% of the total weight of UV photoinitiator 2959, and initiating polymerization under a point light source with a light intensity of 30mW / cm2. All bonding performance tests are i...

Embodiment 2

[0047]

[0048] Dissolve 16g of methyldopamine in 200ml of de-ethanol, fill with nitrogen for 20min, then add 19.8g of acryloyloxybutyl acrylate, react at 35°C for 14 hours until the solution is clear. Ethanol was evaporated with a rotary evaporator to remove the solvent, and the crude product was rinsed with a developing solvent composed of 7:4 dichloromethane:methanol, and the product was subjected to column chromatography to collect the initial fraction. The solvent was distilled off again to obtain 9.6 g of the product. NMR 1 H-NMR identification, 1 H-NMR (DMSO, 600MHz): δ (ppm): 2.27 (CH 3 ); 2.35, 2.65, 2.69, 2.75, 4.15, 4.08 (CH 2 ); 6.42, 6.51 (CH, Ar); 5.80, 6.43 (=CH 2 ); 6.05 (-CH=).

[0049] The product is added with 2% of the total weight of ultraviolet photoinitiator 2959, and the polymerization is initiated under a point light source with a light intensity of 30mW / cm2. All bonding performance tests are all in accordance with the ASTMF225-03 standard, and...

Embodiment 3

[0052]

[0053] Dissolve 9.5g of levodopa in 300ml of ethanol for 20 minutes and add to the reaction system, then add 16.8g of acryloyloxydecyl methacrylate into the reaction system until the solution is uniform. The reaction was kept at 35° C., and after 18 hours of reaction, the by-product was precipitated with cyclohexane, and the solvent was evaporated by rotary evaporation to obtain a crude product. The product was eluted with a developing solvent of ethyl acetate:n-hexane with a ratio of 9:2, and the product was subjected to column chromatography to collect the initial fraction. The solvent was distilled off again to obtain 13.4 g of the product. NMR 1 H-NMR identification, 1 H-NMR (DMSO, 600MHz): δ (ppm): 1.94 (CH 3 ); 2.35, 2.65, 2.69, 2.78, 3.03, 4.15, 4.08 (CH 2 ); 3.88 (CH) 6.42, 6.51 (CH, Ar); 5.58, 6.15 (=CH 2 ).

[0054] The product is added with 2% of the total weight of UV photoinitiator 2959, and the polymerization is initiated under a point light sou...

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Abstract

The invention discloses a photo-curing monomer with ortho-phenolic hydroxyl strucutre, a preparation method and bond thereof. In the formula I monomer, the compound which has crylic acid at two ends or crylic acid double bond at one end and methylacrylic acid double bond at the other end is added to the amidogen of dopamine and derivant thereof through a Michael addition method to form corresponding secondary amine or tertiary amine. In the formula II monomer, the double bond is introduced by (methyl) acrylic anhydride, (methyl) crylic acid and (methyl) acryloyl chloride. The photopolymerization bond comprises the following components by weight percent: 20 to 99.9 percent of the compound with the ortho-phenolic hydroxyl structure, 0 to 70 percent of activated thinner and / or solvent, 0.1 to 10 percent of evocating agent and 0 to 60 percent of natural macromolecule or modified outcome thereof. The bond can be bonded in dry state and wet state, is a quick and long lasting bond, realizes the organic bond of biological bond and photopolymerization, has the advantages of low manufacture cost, simple and convenient operation and high productivity and has extensive application foreground in the biological bond field.

Description

technical field [0001] The invention relates to a photocurable adhesive monomer, its preparation and its application as an adhesive, belonging to the field of adhesives. Background technique [0002] The o-phenolic hydroxyl group of dopamine or its derivatives can form a complex with metal ions in the body. If the o-phenolic hydroxyl group of dopamine or its derivatives is oxidized, or encounters oxidative substances such as tyrosinase in the body, o-quinone is formed The structure of the protein is a substance that can form a covalent cross-linked substance with the protein in the body. This property endows the compound with ortho-phenolic hydroxyl structure with good adhesion in both dry and wet environments. [0003] Photopolymerization (also known as photocuring) technology is a new green technology that came out in the 1960s. Photocuring technology: high efficiency, wide adaptability, economy, energy saving and environmental friendliness. These characteristics endow p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/14C07C229/36C07C227/08C07C233/20C07C233/49C07C231/02C09J4/06
Inventor 杨冬芝牛睿聂俊
Owner BEIJING UNIV OF CHEM TECH
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