CN104803994A - Single-component visible light initiator and preparation method thereof - Google Patents
Single-component visible light initiator and preparation method thereof Download PDFInfo
- Publication number
- CN104803994A CN104803994A CN201510210047.5A CN201510210047A CN104803994A CN 104803994 A CN104803994 A CN 104803994A CN 201510210047 A CN201510210047 A CN 201510210047A CN 104803994 A CN104803994 A CN 104803994A
- Authority
- CN
- China
- Prior art keywords
- visible light
- anthrone
- preparation
- light trigger
- initiator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- ZPJYLOORUVTTBZ-UHFFFAOYSA-N O=C(c1ccc2OCCc2c1)Oc(cc12)ccc1Sc1ccccc1C2=O Chemical compound O=C(c1ccc2OCCc2c1)Oc(cc12)ccc1Sc1ccccc1C2=O ZPJYLOORUVTTBZ-UHFFFAOYSA-N 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Oc(cc1)cc2c1OCO2 Chemical compound Oc(cc1)cc2c1OCO2 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a single-component visible light initiator. The light initiator is prepared by reacting an anthrone derivative with a piperonyl cyclonene derivative. The light initiator solves problems of low visible light utilization rate, smelly initiator system, toxicity, high possibility of yellowing of an existing light initiator; the light initiator has the advantages of simplicity for single-component synthesis, high visible light utilization rate, no toxicity, no yellowing and the like, thereby having huge application potential.
Description
Technical field
The present invention relates to light trigger field, especially relate to visible light initiator of a kind of single component simultaneously containing anthrone structure and piperonyl cyclonene and preparation method thereof.
Background technology
The advantages such as photocuring technology has efficiently, energy-saving and environmental protection, have been widely used in ink, microelectronics and ultra-violet curing coatings art.Light trigger is an important component part of Photopolymer System, because anthrone compounds has synthetic route convenience, low price and efficiency of initiation advantages of higher, has occurred a large amount of commercially produced product efficiently.Isopropyl thioxanthone (trade(brand)name: ITX) is wherein outstanding representative, and its absorbing wavelength is in visible region.Thioxanthone is modal hydrogen-abstraction initiator, does not divide when being in excited state, but extracts a hydrogen from a hydrogen donor molecule, produces a carbonyl radical and a donor free radical, and by the latter's initiated polymerization.Tertiary amine is the most frequently used aided initiating, but emits bad smell after this compounds illumination and there is the problem such as toxicity and xanthochromia.
Cyclic piperonyl compound can extract from natural phant, harmless, good biocompatibility, has very strong resistance of oxidation, is usually used in food, medicine and other fields.The alternative tertiary amine of this compounds is used for photocuring dental material as efficient aided initiating, solves toxicity and the xanthochromia problem (CN101046631A) of tertiary amine existence.By piperonyl cyclonene being introduced directly into the mode of benzophenone skeletal, this compounds also can be used as initiator and is used alone (CN101812141A).There is its own shortcomings in above compound: 1, when cyclic piperonyl compound uses as aided initiating, and bicomponent system exists inverted electron transfer and reduces efficiency of initiation; 2, the dominant absorption wavelength of initiator is at ultraviolet band, low to visible ray utilization ratio, is difficult to match with day by day universal LED light source.
Therefore, development of new, there is one-component, high efficiency visible light initiator just seems extremely important.Sesamol is also piperonyl cyclonene derivative, and methylene radical adjacent with two Sauerstoffatoms in its molecular structure contains reactive hydrogen, has good hydrogen supply capacity, therefore can be used as efficient aided initiating.Specifically, the hydroxyl that sesamol has, is easy to receive on the skeleton of anthrone by molecular modification, synthesizes easy, is beneficial to commercial applications.
Summary of the invention
For the problems referred to above that prior art exists, the applicant provides visible light initiator of a kind of single component and preparation method thereof.Light trigger of the present invention overcomes, the initiator system low to visible ray utilization ratio that existing light trigger exists the problems such as peculiar smell, poisonous, easy xanthochromia, have that synthesis is simple, visible ray utilization ratio is high, nontoxicity and do not bring the advantages such as xanthochromia, there are the potentiality of huge application.
Technical scheme of the present invention is as follows:
A visible light initiator for single component, described light trigger has following general structure:
Wherein, Y is the one in S, N, O, C atom; Z is any one in following several group, and n is integer;
A preparation method for the visible light initiator of single component, described light trigger reacts obtained by anthrone analog derivative and sesamol, and concrete preparation flow is as follows:
Wherein, Y is the one in S, N, O, C.
Described preparation method, comprise the steps: in there-necked flask, add anthrone analog derivative and sesamol, add reaction solvent dry toluene again, dewatering agent dicyclohexylcarbodiimide and catalyzer DMAP, lucifuge back flow reaction is after 10 hours, be spin-dried for solvent, add methylene dichloride and water extraction, get organic phase and spend the night through anhydrous magnesium sulfate drying, after filtering, filtrate concentrates, be separated through column chromatography chromatogram and obtain solid that is colourless or light orange, the described light trigger obtained after vacuum-drying;
The mol ratio of described anthrone analog derivative and sesamol is 1:1 ~ 1.1; The consumption of described dry toluene is 0.2 ~ 0.3moL/L for making reactive component concentration in system.
A preparation method for the visible light initiator of single component, described light trigger is obtained by anthrone analog derivative and piperonyl cyclonene derivatives reaction, and concrete preparation flow is as follows:
Wherein, Y is the one in S, N, O, C; Z is following radicals, and n is integer;
A visible light initiator preparation method for single component, described light trigger is obtained by anthrone analog derivative and piperonyl cyclonene derivatives reaction, and concrete preparation flow is as follows:
Wherein, Y is the one in S, N, O, C.
Described preparation method, comprise the steps: in there-necked flask, add anthrone analog derivative and piperonyl cyclonene derivative, add reaction solvent dry toluene again, lucifuge back flow reaction, after 2 ~ 10 hours, is spin-dried for solvent, adds methylene dichloride and water extraction, get organic phase to spend the night through anhydrous magnesium sulfate drying, after filtering, filtrate concentrates, and is separated obtains solid that is colourless or light orange, the described light trigger obtained after vacuum-drying through column chromatography chromatogram;
The mol ratio of described anthrone analog derivative and piperonyl cyclonene derivative is 1:1 ~ 1.1; The consumption of described dry toluene is 0.2 ~ 0.3moL/L for making reactive component concentration in system.
The visible light initiator of described single component has following structure:
The visible light initiator of described single component has following structure:
The visible light initiator of described single component has following structure:
The technique effect that the present invention is useful is:
1, the light trigger in the present invention contains anthrone group, has larger conjugated structure, wider spectral absorption scope, and extinction wavelength from 200 to 500nm, can mate with conventional LED light source;
2, the light trigger in the present invention is one-component optical initiator, and the two-pack initiator system of light trigger and aided initiating composition can be avoided due to inverted electron transfer to reduce the problem of efficiency of initiation;
3, the piperonyl cyclonene group that the light trigger in the present invention contains, extensively come from natural product, have nontoxic, without xanthochromia, the advantage such as anti-oxidant, that can effectively avoid using the aided initiatings such as amine to bring has the problems such as peculiar smell, easily xanthochromia, has huge commercial application prospect;
4, the light trigger in the present invention has certain photobleaching, and color is thin out gradually in the curing process, is easy to deep cure, and film forming is colourless, non yellowing, has huge commercial application prospect.
Accompanying drawing explanation
Fig. 1 is the embodiment of the present invention 1 gained light trigger synthetic route chart.
Fig. 2 is the embodiment of the present invention 2 gained light trigger synthetic route chart.
Fig. 3 is the embodiment of the present invention 3 gained light trigger synthetic route chart.
Fig. 4 is the embodiment of the present invention 1,2,3 gained light trigger uv-visible absorption spectrum figure;
Wherein, embodiment 1 concentration is 4.5 × 10
-4mol/L (methyl alcohol is solvent), embodiment 2 concentration is 3.8 × 10
-4mol/L (methyl alcohol is solvent), embodiment 3 concentration is 2.7 × 10
-4mol/L (methyl alcohol is solvent).
Fig. 5 is the embodiment of the present invention 1 gained light trigger photobleaching process uv-visible absorption spectrum figure.
Fig. 6 is double bond conversion rate curve in the resin illumination curing process containing the embodiment of the present invention 1,2,3 gained light trigger.
Embodiment
Below in conjunction with drawings and Examples, the present invention is specifically described.
Embodiment 1
With reference to the synthetic route shown in Fig. 1, 2-thioxanthone guanidine-acetic acid 0.27g (1mmol) is taken in single port flask, sesamol is 0.138g (1mmol), add 8mL dry toluene again, dewatering agent dicyclohexylcarbodiimide 0.619g (3mmol), catalyzer DMAP 0.365g (3mmol), lucifuge back flow reaction is after 10 hours, be spin-dried for solvent, add methylene dichloride 10mL and water 10mL to extract, organic phase is spent the night through anhydrous magnesium sulfate drying and is filtered, be separated through column chromatography chromatogram after filtrate concentrates and obtain colourless solid (elutriant: ethyl acetate/petroleum ether=5/1), the target product (productive rate 61%) shown in Fig. 1 is obtained after vacuum-drying, product is as follows through nuclear magnetic resonance spectrum determination structure:
1H NMR(400MHz,CDCl
3)δ8.68-8.60(m,2H)，7.74-7.49(m,6H)，6.79-6.53(m,3H)，5.99(s,2H)，3.99(s,2H)。
The uv-visible absorption spectrum figure of gained light trigger is shown in Fig. 4, as seen from Figure 4, the maximum absorption wavelength in gained light trigger visible-range is 390nm, and absorption region can be extended to 430nm from 320nm, there is wider absorption band, improve the utilization to visible light source.
Gained light trigger photolysis step uv-visible absorption spectrum figure is shown in Fig. 5, and as seen from Figure 5 under light source irradiation, along with the increase of quantity of radiant energy, high wavelength absorption constantly reduces, and illustrates that this initiator has certain photobleaching.
Embodiment 2
With reference to the synthetic route shown in Fig. 2, 2-hydroxyl thioxanthone 0.228g (1mmol) is taken in single port flask, 5-(2-bromotrifluoromethane)-1, 3-benzodioxole is 0.186g (1mmol), add 8mL dry toluene again, lucifuge back flow reaction is after 10 hours, be spin-dried for solvent, add methylene dichloride 10mL and water 10mL to extract, organic phase is spent the night through anhydrous magnesium sulfate drying and is filtered, be separated through column chromatography chromatogram after filtrate concentrates and obtain colourless solid (elutriant: ethyl acetate/petroleum ether=10/1), the target product (productive rate 58%) shown in Fig. 2 is obtained after vacuum-drying, product is as follows through nuclear magnetic resonance spectrum determination structure:
1H NMR(400MHz,DMSO)δ10.18(s,1H)，8.46(m,1H)，7.90-7.52(m,5H)，7.32-7.23(m,1H)。
The uv-visible absorption spectrum figure of gained light trigger is shown in Fig. 4, as seen from Figure 4, the maximum absorption wavelength of gained light trigger visible-range is 405nm, but absorption region can be extended to 450nm from 320nm, there is wider absorption band, improve the utilization to visible light source.
Embodiment 3
With reference to the synthetic route shown in Fig. 3, 2-hydroxyl thioxanthone 0.228g (1mmol) is added in single port flask, pepper acyl chlorides 0.184g (1mmol), add 8mL dry toluene again, lucifuge back flow reaction is after 10 hours, be spin-dried for solvent, add methylene dichloride 10mL and saturated sodium bicarbonate solution 10mL extracts three times, organic phase is spent the night through anhydrous magnesium sulfate drying and is filtered, be separated through column chromatography chromatogram after filtrate concentrates and obtain colourless solid (elutriant: ethyl acetate/petroleum ether=5/1), light trigger of the present invention (productive rate 42%) is obtained after vacuum-drying, product is as follows through nuclear magnetic resonance spectrum determination structure:
1H NMR(400MHz,CDCl
3)δ8.64-8.60(m,1H)，8.42(d,J＝2.5Hz,1H)，7.85(m,1H)，7.64-7.49(m,6H)，6.92(d,J＝8.2Hz,1H)，6.09(s,2H)。
The uv-visible absorption spectrum figure of gained light trigger is shown in Fig. 4, as seen from Figure 4, the maximum absorption wavelength of gained light trigger visible-range is 390nm, but absorption region can be extended to 450nm from 320nm, there is wider absorption band, improve the utilization to visible light source.
Embodiment 4
2-naphthazin(e) ketone group acetic acid 0.252g (1mmol) is added in single port flask, sesamol is 0.138g (1mmol), add 8mL dry toluene, dewatering agent dicyclohexylcarbodiimide 0.619g (3mmol), catalyzer DMAP 0.365g (3mmol), lucifuge back flow reaction is after 10 hours, be spin-dried for solvent, add methylene dichloride 10mL and water 10mL to extract, organic phase is spent the night through anhydrous magnesium sulfate drying and is filtered, be separated through column chromatography chromatogram after filtrate concentrates and obtain colourless solid (elutriant: ethyl acetate/petroleum ether=10/1), light trigger of the present invention (productive rate 38%) is obtained after vacuum-drying.
Embodiment 5
2-hydroxyl xanthone 0.212g (1mmol) is added in single port flask, piperinic acid 0.194g (1.1mmol), add 10mL dry toluene again, dewatering agent dicyclohexylcarbodiimide (0.619g, 3mmol), catalyzer DMAP (0.365g, 3mmol), lucifuge back flow reaction is after 10 hours, be spin-dried for solvent, add methylene dichloride 10mL and water 10mL to extract, organic phase is spent the night through anhydrous magnesium sulfate drying and is filtered, be separated through column chromatography chromatogram after filtrate concentrates and obtain colourless solid (elutriant: ethyl acetate/petroleum ether=5/1), light trigger of the present invention (productive rate 72%) is obtained after vacuum-drying.
Test case:
Accurately take resin Viscoat 295 (TMPTA) 970mg (97wt%), triphenyl phosphorus 20mg (2wt%) and gained light trigger 10mg (1wt%) of the present invention, and mixed, by ultrasonic for the resin mixed 10 minutes to dissolve, to mix, obtained photosensitive resin, keeps in Dark Place stand-by.
1, photocuring test: use happy prestige YW-512020 photocuring system (PHV06-15012 light source, mean power controls at below 2500mW)
Dripped by photosensitive resin and be coated onto slide surface, film thickness monitoring is at about 0.5mm, and controlling irradiation time is 10 seconds.
Adopt the photosensitive resin of embodiment 1 gained light trigger, after illumination, the pencil hardness of film forming is 6H, adopt the photosensitive resin of embodiment 2 gained light trigger, after illumination, the pencil hardness of film forming is 6H (GB/T6739-1996, BY type pencil hardometer (Shanghai Pu Shen chemical machinery company limited)).
2, transformation efficiency test: use Nicolet 6700 FT-IR infrared spectrometer to solidification process Real-Time Monitoring
Dripped by photosensitive resin and be coated onto KBr salt sheet surface, film thickness monitoring is at about 0.5mm, and irradiation time is 300s, and the control intensity of light source is 25mW/cm
2.
Double bond conversion rate in the photosensitive resin of embodiment 1 gained light trigger is adopted to reach 70%, adopt double bond conversion rate in the photosensitive resin of embodiment 2 gained light trigger to reach 75%, adopt double bond conversion rate in the photosensitive resin of embodiment 3 gained light trigger to reach 60%.Double bond conversion rate curve as shown in Figure 6.
Described in embodiment 1, embodiment 2 and embodiment 3, light trigger has all well caused the polymerization of photosensitive resin under light conditions as can be seen from Figure 6, therefore, the aspects such as photo-resist, food product pack, coating, ink can be applied to, and there are the potentiality of commercial applications.
Claims (9)
1. a visible light initiator for single component, is characterized in that described light trigger has following general structure:
Wherein, Y is the one in S, N, O, C atom; Z is any one in following several group, and n is integer;
2. a preparation method for the visible light initiator of single component described in claim 1, it is characterized in that described light trigger reacts obtained by anthrone analog derivative and sesamol, concrete preparation flow is as follows:
Wherein, Y is the one in S, N, O, C.
3. preparation method according to claim 2, is characterized in that comprising the steps:
Anthrone analog derivative and sesamol is added in there-necked flask, add reaction solvent dry toluene again, dewatering agent dicyclohexylcarbodiimide and catalyzer DMAP, lucifuge back flow reaction, after 10 hours, is spin-dried for solvent, adds methylene dichloride and water extraction, get organic phase to spend the night through anhydrous magnesium sulfate drying, after filtering, filtrate concentrates, and is separated obtains solid that is colourless or light orange, the described light trigger obtained after vacuum-drying through column chromatography chromatogram;
The mol ratio of described anthrone analog derivative and sesamol is 1:1 ~ 1.1; The consumption of described dry toluene is 0.2 ~ 0.3moL/L for making reactive component concentration in system.
4. a preparation method for the visible light initiator of single component according to claim 1, it is characterized in that described light trigger is obtained by anthrone analog derivative and piperonyl cyclonene derivatives reaction, concrete preparation flow is as follows:
Wherein, Y is the one in S, N, O, C; Z is following radicals, and n is integer;
5. a preparation method for the visible light initiator of single component according to claim 1, it is characterized in that described light trigger is obtained by anthrone analog derivative and piperonyl cyclonene derivatives reaction, concrete preparation flow is as follows:
Wherein, Y is the one in S, N, O, C.
6. the preparation method according to claim 4 or 5, is characterized in that comprising the steps:
Anthrone analog derivative and piperonyl cyclonene derivative is added in there-necked flask, add reaction solvent dry toluene again, lucifuge back flow reaction is after 2 ~ 10 hours, be spin-dried for solvent, add methylene dichloride and water extraction, get organic phase and spend the night through anhydrous magnesium sulfate drying, after filtering, filtrate concentrates, be separated through column chromatography chromatogram and obtain solid that is colourless or light orange, the described light trigger obtained after vacuum-drying;
The mol ratio of described anthrone analog derivative and piperonyl cyclonene derivative is 1:1 ~ 1.1; The consumption of described dry toluene is 0.2 ~ 0.3moL/L for making reactive component concentration in system.
7. the visible light initiator of single component according to claim 1, is characterized in that having following structure:
8. the visible light initiator of single component according to claim 1, is characterized in that having following structure:
9. the visible light initiator of single component according to claim 1, is characterized in that having following structure:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510210047.5A CN104803994A (en) | 2015-04-28 | 2015-04-28 | Single-component visible light initiator and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510210047.5A CN104803994A (en) | 2015-04-28 | 2015-04-28 | Single-component visible light initiator and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104803994A true CN104803994A (en) | 2015-07-29 |
Family
ID=53689223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510210047.5A Pending CN104803994A (en) | 2015-04-28 | 2015-04-28 | Single-component visible light initiator and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104803994A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243251A (en) * | 2016-08-23 | 2016-12-21 | 江南大学 | A kind of one pack system visible light initiator and in the application of hybrid UV-curing |
| CN110078719A (en) * | 2019-05-24 | 2019-08-02 | 江南大学 | A kind of cumarin-sesamol biology base photoinitiator and preparation method thereof |
| CN110498870A (en) * | 2019-07-17 | 2019-11-26 | 山东科技大学 | A method of PMMA microsphere is prepared using natural material |
| CN115286641A (en) * | 2022-08-29 | 2022-11-04 | 江南大学 | Thioxanthone single-component visible light initiator and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2418834A1 (en) * | 1974-04-19 | 1975-10-30 | Hoechst Ag | LIGHT-DEGRADABLE THERMOPLASTIC MOLDING COMPOUNDS |
| CN103880987A (en) * | 2014-04-02 | 2014-06-25 | 长沙新宇高分子科技有限公司 | Thioxanthone photoinitiators and preparation method thereof |
-
2015
- 2015-04-28 CN CN201510210047.5A patent/CN104803994A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2418834A1 (en) * | 1974-04-19 | 1975-10-30 | Hoechst Ag | LIGHT-DEGRADABLE THERMOPLASTIC MOLDING COMPOUNDS |
| CN103880987A (en) * | 2014-04-02 | 2014-06-25 | 长沙新宇高分子科技有限公司 | Thioxanthone photoinitiators and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| JINLIANG YANG 等: "Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator", 《PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES》 * |
| 杨金梁 等: "环缩醛化合物在光聚合体系中的研究进展", 《影像科学与光化学》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243251A (en) * | 2016-08-23 | 2016-12-21 | 江南大学 | A kind of one pack system visible light initiator and in the application of hybrid UV-curing |
| CN106243251B (en) * | 2016-08-23 | 2018-07-03 | 江南大学 | A kind of one pack system visible light initiator and the application in hybrid UV-curing |
| CN110078719A (en) * | 2019-05-24 | 2019-08-02 | 江南大学 | A kind of cumarin-sesamol biology base photoinitiator and preparation method thereof |
| CN110498870A (en) * | 2019-07-17 | 2019-11-26 | 山东科技大学 | A method of PMMA microsphere is prepared using natural material |
| CN115286641A (en) * | 2022-08-29 | 2022-11-04 | 江南大学 | Thioxanthone single-component visible light initiator and preparation method and application thereof |
| CN115286641B (en) * | 2022-08-29 | 2023-11-24 | 江南大学 | Thioxanthone single-component visible light initiator and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104803994A (en) | Single-component visible light initiator and preparation method thereof | |
| Kumbaraci et al. | Naphthodioxinone‐1, 3‐benzodioxole as photochemically masked one‐component type II photoinitiator for free radical polymerization | |
| KR101742473B1 (en) | Carbazole ketoxime ester high-photosensitivity photoinitiator | |
| CN104817653A (en) | Coumarin oxime ester photoinitiator and preparation method thereof | |
| MY142016A (en) | Antireflective compositions for photoresists | |
| CN102834372A (en) | Amine synergists and application inradiation curing | |
| CN104761661B (en) | A kind of water soluble Benzophenone-type light initiator of polymerizable and preparation method thereof | |
| CN101130518A (en) | Ionic liquid photo generated base alkaline agent, preparing method and uses of the same | |
| CN105107545A (en) | Application of ionic liquid catalyst | |
| CN107814694A (en) | Fluorenes class initiator, its preparation method, the Photocurable composition with it and its application in curing field | |
| CN103205183A (en) | Tasteless and nontoxic aqueous ultraviolet-curable coating and preparation method thereof | |
| Deng et al. | Synthesis and properties of novel bis-chalcone-based photoinitiators for LED polymerization with photobleaching and low migration | |
| CN104844564A (en) | Latent type photoinduced decarboxylation photobase generator and preparation method thereof | |
| CN104098720A (en) | Oxime ester photoinitiator containing heterocyclic thioether group as well as preparation method and application thereof | |
| CN105153329B (en) | Acetophenone type photoinitiators using fluorene as conjugated structure as well as preparation method and application of acetophenone type photoinitiators | |
| Tani et al. | Chiral Helicenoid Diarylethene with Highly Diastereoselective Photocyclization1 | |
| CN105152898A (en) | Phenylbutanone derivative and application of same as photoinitiator | |
| CN106278967A (en) | For the acyl group oxime ester compound of UV curing materials and synthetic method thereof and application | |
| CN114716315A (en) | Application of aromatic vinyl alpha-carbonyl acid ester compound as photoinitiator in LED photopolymerization and preparation method thereof | |
| CN106278966B (en) | Oxime ester compound and its synthetic method and application | |
| CN106146689A (en) | A kind of aqueous host and guest's build light trigger and preparation method thereof | |
| CN102766045A (en) | Benzophenone derivative and application thereof as photoinitiator | |
| CN107129714B (en) | A kind of preparation method of soybean oil acrylate type UV-cured resin | |
| Zhang et al. | Naphthoquinone-Based Oxime Esters for Free Radical Photopolymerization under Sunlight or a Blue Light-Emitting Diode | |
| Wang et al. | Benzophenone-1, 3-dioxane as a free radial initiator for photopolymerization |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| EXSB | Decision made by sipo to initiate substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150729 |