Photo-bleachable visible light initiator as well as preparation method and application thereof

A technology of visible light and initiator, which is applied in the field of photobleachable visible light initiator and its preparation, can solve the problems of reduced curing depth of curing system and reduced visible light penetration, and achieves simple synthesis method, wide applicability and matching reasonable effect

Active Publication Date: 2020-04-03
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the problem that the curing system absorbs visible light during the visible light curing process in the prior art, the penetration of visible light is reduced and the curing depth of the curing system is reduced. The purpose of the present invention is to provide a photobleachable visible light initiator.

Method used

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  • Photo-bleachable visible light initiator as well as preparation method and application thereof
  • Photo-bleachable visible light initiator as well as preparation method and application thereof
  • Photo-bleachable visible light initiator as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0046] [Example 2] Preparation of photobleachable visible light initiator shown in formula 2

[0047]

[0048] Add 2-allyl-4-diethylaminobenzaldehyde (0.217g, 1mmol) in 100mL single-necked flask, cyclohexylamine (0.1g, 1mmol), diethyl malonate (0.216g, 1mmol), Glacial acetic acid (0.06g, 1mmol), 10g of toluene, heated up to 100°C for 48h under the protection of argon, the raw materials were almost completely reacted by TCL, the low boiling point was removed under reduced pressure, diluted by adding PE:EA=10:1, centrifuged, The supernatant was passed through a silica gel column (PE:EA=10:1) to obtain a yellow transparent liquid, which was a photobleachable visible photoinitiator. 1 H NMR (400MHz, CDCl 3 )δ8.62(s,1H,-C=CH-Ar),7.28(d,J=8.7Hz,1H,Ar-H),7.20(dd,J=14.2,6.6Hz,2H,Ar-H) ,5.92(dd,J=16.8,7.8Hz,1H,-CH 2 CH=CH 2 ),5.04(d,J=8.7Hz,2H,-CH 2 CH=CH 2 ),4.29–4.18(m,4H,-OCH 2 CH 3 ),3.36(q,J=7.1Hz,4H,-NCH 2 CH 3 ),3.14–2.96(m,2H,-CH 2 CH=CH 2 ), 1.23 (dt, J=11.7, 7....

Embodiment 3

[0049] [embodiment 3] the preparation of photobleachable visible light initiator shown in formula 3

[0050]

[0051] Sodium hydride (0.072g, 3mmol) was added to a 100mL single-necked flask, placed in an ice-water bath, and 2,4-diethylaminobenzaldehyde (0.248g, 1mmol) was slowly added dropwise under the protection of argon, anhydrous ethyl acetate Ester (0.55g, 3mmol), mixed solution of anhydrous tetrahydrofuran 5.0g, dropwise addition was completed in 30min, reacted in an ice-water bath for 12h, TCL detected that the raw material had reacted completely, removed the low boiling point under reduced pressure, added PE:EA=10:1 to dilute, after Silica gel column (PE:EA=10:1) gave yellow transparent oily liquid. 1 H NMR (400MHz, CDCl 3 )δ8.08(d,J=16.1Hz,1H,-C=CH-Ar),7.65–7.36(m,1H,Ar-H),6.43–6.33(m,1H,Ar-H),6.30( d,J=2.6Hz,1H,HC=C-),6.19(d,J=16.0Hz,1H,Ar-H),4.35–4.14(m,2H-OCH 2 CH 3 ),3.37(q,J=7.1Hz,4H,-NCH 2 CH 3 ), 3.04 (q, J=7.1Hz, 4H, NCH 2 CH 3 ), 1.31 (q, J=7.2Hz, ...

Embodiment 6

[0058] [embodiment 6] the preparation of photobleachable visible light initiator shown in formula 6

[0059]

[0060] Add 2,4-bis-(diethylamino)benzaldehyde (0.248g, 1mmol) in 100mL single-necked flask, cyclohexylamine (0.1g, 1mmol), 1,3-indenedione (0.146g, 1mmol), Glacial acetic acid (0.06g, 1mmol), 10g of toluene, under the protection of argon at room temperature for 12h, the raw materials were almost completely reacted by TCL, the low boiling was removed under reduced pressure, diluted by adding PE:EA=10:1, centrifuged, and the supernatant was passed through Silica gel column (PE:EA=10:1) to obtain a red solid powder is photobleachable visible light initiator. 1 H NMR (400MHz, CDCl 3 )δ9.12–8.87(m,1H,-C=CH-),8.18(s,1H,Ar-H),7.96–7.69(m,2H,Ar-H),7.69–7.42(m,2H, Ar-H), 6.34(dt, J=22.3, 11.2Hz, 1H, Ar-H), 6.11(dd, J=12.0, 2.5Hz, 1H, Ar-H), 3.47–3.26(m, 4H,- NCH 2CH 3 ), 3.11 (q, J=7.1Hz, 4H, -NCH 2 CH 3 ),1.22–1.12(m,6H,-NCH 2 CH 3 ), 1.07(t, J=7.1Hz, 6H, -NCH 2 ...

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Abstract

The invention discloses a photo-bleachable visible light initiator as well as a preparation method and application thereof, and belongs to the field of visible light photocuring. In the prior art, inthe visible light photocuring process, a curing system can absorb visible light, so that the penetrability of visible light is reduced, and the curing depth of the curing system is reduced. The photo-bleachable visible light initiator provided by the invention can successfully initiate visible light free radical photopolymerization, and a polymerized material can be changed from colored to colorless and transparent, so that the material application range is widened, and the curing depth is increased. The invention also provides a preparation method of the photo-bleachable visible light initiator. According to the preparation method, an aromatic aldehyde and a compound containing active methylene are subjected to condensation reaction to prepare the photo-bleachable visible light initiator.The synthesis method of the photo-bleachable visible light initiator is simple, the absorption wavelength of the photo-bleachable visible light initiator can be adjusted and changed through molecularstructure adjustment to adapt to light sources with different wavelengths, and the application range is wide.

Description

technical field [0001] The invention belongs to the technical field of visible light curing, and in particular relates to a photobleachable visible light initiator and a preparation method and application thereof. Background technique [0002] Light curing technology has the characteristics of low energy consumption, low pollution, high efficiency, fast room temperature, and complete curing. It is a kind of green environmental protection technology and can be widely used in inks, coatings, photoresistors, adhesives, printed circuit printing etc. As an important part of photocurable materials, photoinitiators not only determine the speed and degree of photocuring, but also affect the performance of photocurable products. High optical density and high strength are the keys to the commercial success of UV curing technology. Although UV curing technology has been widely used in many fields, there are certain inherent defects in this technology, such as ozone generation, insuff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/10C07C229/44C07C253/30C07C255/42C07C255/37C07C221/00C07C225/22C07C201/12C07C205/42C07C45/74C07C49/255C07C315/04C07C317/18C07C67/293C07C69/54C07D295/135C07D307/79C07D333/66C07D333/56C07D209/88C07D209/86C07D209/12C08F2/48
CPCC07C45/74C07C67/293C07C201/12C07C221/00C07C227/10C07C253/30C07C315/04C07D209/12C07D209/86C07D209/88C07D295/135C07D307/79C07D333/56C07D333/66C08F2/48C07C2601/10C07C2601/14C07C2602/08C07C229/44C07C255/42C07C255/37C07C225/22C07C205/42C07C49/255C07C317/18C07C69/54
Inventor 唐红定廖文熊英
Owner WUHAN UNIV
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