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Modified benzophenone photo-initiator and preparation method thereof

A technology of benzophenone and photoinitiator, which is applied in the field of benzophenone photoinitiator and its preparation, can solve the problems of easy migration, decreased solubility, and restrictions on the application of photocuring systems, so as to accelerate the photopolymerization reaction , avoid the decrease of solubility, and curb the effect of oxygen inhibition

Inactive Publication Date: 2016-02-10
安徽皖科新科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the small molecule photoinitiator of diphenyl ketone has shown some disadvantages when it is used: due to its low boiling point, small molecular weight, strong volatility, and easy migration, the residual photoinitiator and photolysis products will flow to the system after curing. The migration of the surface layer affects the appearance and performance of the coating (such as toxicity and yellowing); the smell is large (the photolysis product has an odor), these shortcomings restrict the wider application of the photocuring system (such as food and pharmaceutical packaging, etc. Applications)
The increase of the molecular weight of the photoinitiator can overcome the shortcomings of the small molecule photoinitiator such as easy migration, volatilization and odor to a certain extent, but at the same time, there is a possibility of entanglement of the intermolecular chains due to the growth of the molecular chains, thus Resulting in a decrease in solubility that ultimately affects its use

Method used

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  • Modified benzophenone photo-initiator and preparation method thereof
  • Modified benzophenone photo-initiator and preparation method thereof
  • Modified benzophenone photo-initiator and preparation method thereof

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preparation example Construction

[0031] The preparation method of the modified benzophenone photoinitiator of a kind of formula (I) proposed by the present invention, comprises the steps:

[0032] (a) get 2-(benzoyl) benzoic acid (339.2g, 1.5mol) and join in the 1000ml three-necked flask filled with 300ml of toluene, stir and dissolve at 60 DEG C, slowly add dichlorosulfuric acid dropwise to this mixed system Sulfone (111.2ml, 1.5mol), refluxed for 6 hours after the dropwise addition, the solvent toluene was removed by rotary evaporation to a colorless liquid (342.6g), which was 2-(benzoyl)benzoyl chloride, the intermediate Compound II, the yield was 93.3%.

[0033] 1 HNMR (300MHz, CDCl 3 ): δ8.32 (d, 1H, -CHCCOCl), δ7.81 (d, 2H, -CHCCO), δ8.03 (d, 1H, -CHCCO), δ7.61-7.73 (m, 3H).

[0034] Elemental analysis: (C 14 H 9 ClO 2 )

[0035]

Embodiment 1

[0037] (b) Pentaerythritol (34.1 g, 0.25 mol) was added to a 500 ml three-necked flask containing 200 ml of 1,2-dichloroethane, and 100 ml of triethylamine was added simultaneously. Take the product 2-(benzoyl)benzoyl chloride (244.8g, 1mol) in step (a) and slowly add it dropwise to the above mixed system, stir and react at 40°C for 12 hours, filter, and remove by rotary evaporation Solvent 1,2-dichloroethane to obtain 231.7 g of colorless liquid, which is one of the products of the present invention: I-1 or G-BP-4, with a yield of 83.8%.

[0038] 1 HNMR (300MHz, CDCl 3 ): δ4.21(s, 8H, -CH 2 ), δ8.28(d, 4H, -CHCCOO), δ7.81(d, 8H, -CHCCO), δ8.01(d, 4H, o-phCOO), δ8.45(t, 4H, p-phCOO ).

[0039] Elemental analysis: (C 61 H 44 O 12 )

[0040]

Embodiment 2

[0042](b) Methylolpropane (33.5g, 0.25mol) was added to a 500ml three-necked flask containing 200ml of 1,2-dichloroethane, and 100ml of triethylamine was added simultaneously. Take the product 2-(benzoyl)benzoyl chloride (183.6g, 0.75mol) in step (a) and slowly add it dropwise to the above mixed system, stir and react at 40°C for 12 hours, filter, and rotate by evaporation The solvent 1,2-dichloroethane was removed to obtain 170.1 g of a colorless liquid, which was one of the products of the present invention: I-2 or G-BP-3, with a yield of 88.6%.

[0043] 1 HNMR (300MHz, CDCl 3 ): δ0.93 (t, 3H, -CH 3 ), δ1.73 (q, 2H, -CH 2 CH 3 ), δ4.59(s, 6H, -CH 2 ), δ7.83 (d, 6H, -CHCCO), δ8.18 (d, 3H, o-phCOO), δ8.41 (t, 3H, p-phCOO).

[0044] Elemental Analysis (C 48 H 38 O 9 ):

[0045]

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Abstract

The invention discloses a modified benzophenone photo-initiator represented by a formula (I). In the formula, R is polyol residue, R1 is hydrogen or methyl or ethyl or other small-molecular organic groups. According to the novel benzophenone photo-initiator, polyol is adopted as a connection agent connecting a plurality of benzophenone molecules in a molecule, such that the photo-initiator with relatively large molecular weight and with a star or spherical structure is obtained. With the star or spherical structure, large molecular weight and a large number of photoactive groups in the molecule, the photo-initiator provided by the invention has high initiation efficiency. Defects of easy migration, high odor and oxygen polymerization inhibition of single small-molecular benzophenone photo-initiators can be effectively solved. With the excellent comprehensive performances, the photo-initiator can be put in an important position in future light curing market.

Description

technical field [0001] The present invention relates to a benzophenone-based photoinitiator with star-shaped or spherical molecular structure and a preparation method thereof. Background technique [0002] Photoinitiator (PI) is an extremely important component of the photocuring system, which is directly related to whether the oligomer and diluent can be rapidly transformed from liquid to solid when the photocurable formulation system is irradiated with light, that is, cross-linking. Co-curing and directly affect many physical and chemical properties of the cured system (such as mechanical properties, yellowing, odor, etc.). [0003] At present, the photoinitiators used in the market are mainly monofunctional small-molecule photoinitiators. Among them, the benzophenone small-molecule photoinitiators are widely used due to their low preparation cost and simple preparation method. One of the photoinitiators. However, the benzophenone small molecule photoinitiator has shown ...

Claims

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Application Information

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IPC IPC(8): C08F2/48C07C69/76C07C67/14
Inventor 徐会君李淳鲁祥勇
Owner 安徽皖科新科技发展有限公司
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