A kind of photobleachable visible light initiator and its preparation method and application

A visible light and initiator technology, applied in the field of photobleachable visible light initiator and its preparation, can solve the problems of reduced curing depth of curing system, reduced visible light penetration and the like, and achieves simple synthesis method, wide applicability and cheap raw materials. easy-to-get effect

Active Publication Date: 2021-03-16
WUHAN UNIV
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  • Summary
  • 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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  • A kind of photobleachable visible light initiator and its preparation method and application
  • A kind of photobleachable visible light initiator and its preparation method and application
  • A kind of photobleachable visible light initiator and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0046] [Example 2] Preparation of the photobleachable visible light initiator represented by formula 2

[0047]

[0048] 2-allyl-4-diethylaminobenzaldehyde (0.217g, 1mmol), cyclohexylamine (0.1g, 1mmol), diethyl malonate (0.216g, 1mmol) were added to the 100mL single-necked flask, Glacial acetic acid (0.06g, 1mmol), 10g of toluene, heated to 100°C for 48h under the protection of argon, TCL detected that the reaction of the raw materials was almost complete, removed the low boiling point under reduced pressure, added PE:EA=10:1 to dilute, centrifuged, The supernatant liquid is passed through a silica gel column (PE:EA=10:1) to obtain a yellow transparent liquid, which is a visible light photobleachable initiator. 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 ...

Embodiment 3

[0049] [Example 3] Preparation of the photobleachable visible light initiator represented by formula 3

[0050]

[0051] Sodium hydride (0.072g, 3mmol) was added to a 100mL single-necked flask, placed in an ice-water bath, 2,4-diethylaminobenzaldehyde (0.248g, 1mmol) was slowly added dropwise under the protection of argon, anhydrous ethyl acetate The mixed solution of ester (0.55g, 3mmol) and 5.0g of anhydrous tetrahydrofuran was added dropwise in 30min, reacted in ice-water bath for 12h, TCL detected that the reaction of the raw materials was complete, removed the low boiling point under reduced pressure, added PE:EA=10:1 to dilute, after Silica gel column (PE:EA=10:1) gave a 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=7.2...

Embodiment 6

[0058] [Example 6] Preparation of the photobleachable visible light initiator represented by formula 6

[0059]

[0060] 2,4-bis-(diethylamino)benzaldehyde (0.248g, 1mmol), cyclohexylamine (0.1g, 1mmol), 1,3-indanedione (0.146g, 1mmol) were added to the 100mL single-necked flask, Glacial acetic acid (0.06g, 1mmol), 10g of toluene, under the protection of argon at room temperature for 12h, TCL detected that the reaction of the raw materials was almost complete, removed the low boiling point under reduced pressure, added PE:EA=10:1 for dilution, centrifuged, and the supernatant was passed through The red solid powder obtained by silica gel column (PE:EA=10:1) is the visible light initiator that can be photobleached. 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,...

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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. printing, etc. As an important part of photocurable materials, photoinitiator not only determines the speed and degree of photocuring, but also affects the performance of photocurable products. Large optical density and high intensity are the keys to the commercial success of UV curing technology. Although UV curing technology has been widely used in many fields, this technology has certain inherent defects, such as ozone generation, insufficient curing depth, etc., and long-term UV light irradiation will cause great harm to the human body. [0003] These problems can be solved by usi...

Claims

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Application Information

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Patent Type & Authority Patents(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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