CN101942046A - Benzophenone fragment and p-nitrodiphenylethene fragment-containing tree like visible light photoinitiator and synthesis and application thereof - Google Patents
Benzophenone fragment and p-nitrodiphenylethene fragment-containing tree like visible light photoinitiator and synthesis and application thereof Download PDFInfo
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- CN101942046A CN101942046A CN 201010281723 CN201010281723A CN101942046A CN 101942046 A CN101942046 A CN 101942046A CN 201010281723 CN201010281723 CN 201010281723 CN 201010281723 A CN201010281723 A CN 201010281723A CN 101942046 A CN101942046 A CN 101942046A
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Abstract
The invention relates to a benzophenone fragment and p-nitrodiphenylethene fragment-containing tree like visible light photoinitiator and synthesis and application thereof, belonging to the field of photoinitiators. The tree like visible light photoinitiator comprises the typical chemical structural general formulae shown in the description, wherein n1 and n2 in molecular structural formulae (I) and (II) represent 1-6, wherein in the molecular structural formula (I), the (I) is prepared through reacting 4-(4'-bromohydrocarbylstyyl) nitrobenzene with 3,5-dihydroxylbenzyl alcohol to obtain a product of 3,5-di((4'-nitrobenzenevinyl)benzene alkoxide)benzyl alcohol, and then reacting the 3,5-di((4'-nitrobenzenevinyl)benzene alkoxide)benzyl alcohol with 4-bromomethylbenzophenone under alkaline conditions; and in the molecular structural formula (II), the (II) is prepared through reacting 4-bromohydrocarbylbenzophenone with 3,5-dihydroxylbenzyl alcohol to obtain a product of 3,5-di((4'-benzoyl)benzene alkoxide)benzyl alcohol, and then reacting the 3,5-di((4'-benzoyl)benzene alkoxide)benzyl alcohol with 4-(4'-hydroxylstyryl)nitrobenzene under alkaline conditions. The benzophenone fragment and p-nitrodiphenylethene fragment-containing tree like visible light photoinitiator has the maximum absorption in a visible light region and can be used as the photoinitiator to form a photosensitive system together with a triethanolamine auxiliary agent and used for visible light polymerization of alkene monomers in a solution or used as photocuring materials.
Description
Technical field
The invention belongs to the visible light initiator field, particularly contain benzophenone fragment and the segmental dendritic visible light light trigger of nitro toluylene.
Background technology
Long wavelength laser such as Ar+ (488nm in recent years, 514nm), YAG (532nm), He-Ne (633nm) be in the widespread use in fields such as Computer To Plate, photocuring, double photon photopolymerization and high-density digital optical storage, make to develop the key areas that visible light light trigger efficiently becomes present optical information research.One of them method is that ultraviolet initiator is connected on the visible dyes by valence bond.Koichi Kawamura has found that ultraviolet initiator three chloro s-triazine are connected on the visible light cyanine dyes and can bring up to 500-600nm to absorb light, exercise question is: " synthetic two (the three chloro methyl)-1 that are connected with new dyestuff of appraisal, 3, the 5-triazine is as the visible light Photoepolymerizationinitiater initiater " (Synthesis and evaluation as avisible-light polymerization photoinitiator of a new dye-linked bis (trichloromethyl)-1,3,5-triazine), " Polymers for Advanced Technologies " (polymkeric substance that is used for hi-tech), 2004,15 (6), 324-328.The polymerization of photic transfer transport generation free radical initiation vinyl monomer takes place in three chloro s-triazine and visible light cyanine dyes under visible light illumination.Yet this compounds synthesis step is various, efficiency of initiation is not high, and three chloro s-triazine illumination often produce obnoxious flavoures such as chlorine, therefore can be subjected to a lot of restrictions in actual applications.Benzophenone is business-like ultraviolet initiator, but its absorbing wavelength is very short, and between 250-300nm, visible region does not almost absorb.And contain benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene, and its maximum absorption is at visible region, and has bigger molar extinction coefficient, and range of application has obtained expansion.
Summary of the invention
The present invention contains benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene, not only can itself absorb visible light, and can have the visible light initiating power, and can improve the light-initiated efficient of visible light by the preparation of easy method.
Involved in the present invention contain benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene, the typical chemical structure of general formula of its compound is as follows:
N in the molecular structural formula (I), (II) wherein
1And n
2All represent 1-6.
Above-mentionedly contain benzophenone fragment and the synthetic method of the segmental dendritic visible light light trigger of nitro toluylene (I) be may further comprise the steps:
Synthesizing of (1) 3,5-two ((4 '-nitrostyrolene base) benzene-oxyl) phenylcarbinol
Reaction equation:
Concrete steps:
Compound with structural formula (III) representative, with 3,5-dihydroxybenzyl alcohol, basic catalyst join in there-necked flask with mol ratio and mix at 3: 1: 2, then with an amount of anhydrous propanone dissolving, stir about is 12 hours under the room temperature, filters out precipitation, the filtrate decompression distillation, adopt silicagel column separate yellow compound, standby;
(2): contain benzophenone fragment and to the building-up reactions equation of the segmental dendritic visible light light trigger of nitro toluylene (I):
Concrete steps:
With the first step make 3,5-two ((4 '-nitrostyrolene base) benzene-oxyl) phenylcarbinol, join in there-necked flask at 1: 1.5: 1 with mol ratio with 4-brooethyl benzophenone, basic catalyst and to mix, then with an amount of anhydrous propanone dissolving, stir about is 12 hours under the room temperature, filter out precipitation, filtrate decompression distillation, adopt silicagel column separate yellow compound.
Above-mentionedly contain benzophenone fragment and the synthetic method of the segmental dendritic visible light light trigger of nitro toluylene (II) be may further comprise the steps:
Synthesizing of (1) 3,5-two ((4 '-benzoyl) benzene-oxyl) phenylcarbinol
Reaction equation:
Concrete steps:
Compound with structural formula (IV) representative, with 3,5-dihydroxybenzyl alcohol, basic catalyst join in there-necked flask with mol ratio and mix at 3: 1: 2, then with an amount of anhydrous propanone dissolving, stir about is 12 hours under the room temperature, filters out precipitation, the filtrate decompression distillation, adopt silicagel column separate the whitening compound, standby;
Synthesizing of (2) 3,5-two ((4 '-benzoyl) benzene-oxyl) benzyl bromine
Reaction equation:
Concrete steps:
With second the step make 3,5-two ((4 '-benzoyl) benzene-oxyl) benzyl bromine and phosphorus tribromide join in the there-necked flask with 1: 1.5 mol ratio and mix, then with an amount of anhydrous tetrahydro furan dissolving, stir about is 30 minutes under the room temperature, wash twice, adopt silicagel column separate the whitening compound, standby;
(3): contain benzophenone fragment and synthesizing to the segmental dendritic visible light light trigger of nitro toluylene (II)
Reaction equation:
Concrete steps:
With second the step make 3; 5-two-((4 '-benzoyl) benzene-oxyl) benzyl bromine joins in there-necked flask with mol ratio with 4-(4 '-hydroxystyrene based) oil of mirbane, basic catalyst and mixes at 1: 1.5: 1; then with an amount of anhydrous propanone dissolving; stir about is 12 hours under the room temperature; filter out precipitation; filtrate decompression distillation, adopt silicagel column separate yellow compound.
Described basic catalyst is sodium hydride, sodium alkoxide, potassium alcoholate or their any mixture.
Of the present invention contain benzophenone fragment and the segmental dendritic visible light light trigger of nitro toluylene mixed with the trolamine auxiliary agent can form photosensitized initiation system, and because its absorption bands is wide, absorbing wavelength is at visible region, can with now all visible light source such as tungsten-iodine lamp, xenon lamp, Ar
+Laser apparatus, YAG (532nm) laser apparatus etc. are complementary.Therefore, dye molecule of the present invention and trolamine auxiliary agent can be used for the visible light photopolymerization of vinyl monomer in the solution.
Photosensitizers consumption, configuration and the using method of dyestuff of the present invention during as above purposes is as follows:
Vinyl monomer: 25%-80wt%
Organic solvent: 25%-80wt%
Contain benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene (light trigger of the present invention): 0.01%-10wt%
Trolamine auxiliary agent: 0.01%-10wt%
The concrete operations step is as follows:
In the long horminess glass tube of 10cm, the organic solvent that adds 10%-80wt%, the vinyl monomer of 25%-80wt%, 0.01%-10wt% contain benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene (light trigger of the present invention), the trolamine auxiliary agent of 0.01%-10wt%, the logical argon gas 20-30 minute deoxygenation of lucifuge then.At room temperature use visible light apart from 5cm, stirred illumination 0.5-6 hour down.With cold methyl alcohol polymkeric substance is separated out, promptly get thick product.Carry out precipitation process again, can obtain the purified alkene monomer polymer.
In the above-mentioned prescription, described vinyl monomer comprises acrylic acid or the like, acrylamide, vinyl cyanide, styrenic, vinyl-acetic ester class or their any miscellany.
Described organic solvent comprises ester class, ethers, acetonitrile or their any miscellanys.
Involved in the present invention contains benzophenone fragment and the segmental dendritic visible light light trigger of nitro toluylene is had following advantage:
(1) of the present invention contain benzophenone fragment with to the synthetic method of the segmental dendritic visible light light trigger of nitro toluylene and separate simple to operationly, raw material sources conveniently are easy to get, and per step productive rate is fit to.
(2) of the present inventionly contain benzophenone fragment and the segmental dendritic visible light light trigger absorption bands of nitro toluylene is covered broad.
(3) of the present inventionly contain benzophenone fragment and the segmental dendritic visible light light trigger of nitro toluylene is had good fluorescent emission ability.
(4) of the present inventionly contain benzophenone fragment and itself not only can absorb visible light, because contain benzophenone simultaneously and, have light initiation polymerization efficient efficiently to nitro diphenyl ethylene to the segmental dendritic visible light light trigger of nitro toluylene.
Description of drawings
Fig. 1. the embodiment of the invention 3 is 3, and 5-two (4 ' (4 '-nitrostyrolene base) benzyloxy)-1-(4 '-benzoyl benzyloxy methylene radical) benzene is dissolved in the relation curve of absorbancy and wavelength in the methylene dichloride.
Fig. 2. the embodiment of the invention 4 is 3, and 5-two (4 '-benzoyl benzyloxy)-1-(4 ' (4 '-nitrostyrolene base) phenoxy group methylene radical) benzene is dissolved in the relation curve of absorbancy and wavelength in the acetonitrile.
Embodiment
Embodiment 1
3,5-two (4 ' (4 '-nitrostyrolene base) benzyloxy)-1-(4 '-benzoyl benzyloxy methylene radical) benzene synthetic
Synthesizing of (1) 3,5-two ((4 '-nitrostyrolene base) benzyloxy) phenylcarbinol
With 4-(4 '-brooethyl styryl) oil of mirbane 13.6g and 2.0g 3,5-dihydroxybenzyl alcohol, 3.9g K
2CO
3(mol ratio 3: 1: 2) joins in the there-necked flask and mixes, and with the dissolving of an amount of anhydrous propanone, stirs 12 hours under the room temperature then, filters out precipitation, the filtrate decompression distillation, adopt silicagel column separate yellow compound, productive rate is 56%, and is standby;
Synthesizing of (2) 3,5-two (4 ' (4 '-nitrostyrolene base) benzyloxy)-1-(4 '-benzoyl benzyloxy methylene radical) benzene
The 4.0g 3 that the first step is made, 5-two ((4 '-nitrostyrolene base) benzyloxy) phenylcarbinol, join in the there-necked flask and mix with 2.7g 4-brooethyl benzophenone, 0.16g NaH (mol ratio 1: 1.5: 1), then with an amount of anhydrous propanone dissolving, stirred 12 hours under the room temperature, filter out precipitation, the filtrate decompression distillation, adopt silicagel column separate yellow compound, productive rate 52%.
Embodiment 2
3,5-two (4 '-benzoyl benzyloxy)-1-(4 ' (4 '-nitrostyrolene base) phenoxy group methylene radical) benzene synthetic
Synthesizing of (1) 3,5-two ((4 '-benzoyl) benzyloxy) phenylcarbinol
With 4-brooethyl benzophenone 11.8g and 2.0g 3,5-dihydroxybenzyl alcohol, 3.9g K2CO3 (mol ratio 3: 1: 2) join in the there-necked flask and mix, then with an amount of anhydrous propanone dissolving, stirred 12 hours under the room temperature, filter out precipitation, filtrate decompression distillation, adopt silicagel column separate the whitening compound, productive rate is 61%, and is standby;
Synthesizing of (2) 3,5-two ((4 '-benzoyl) benzyloxy) benzyl bromine
With the first step make 3,5-two ((4 '-benzoyl) benzyloxy) phenylcarbinol 4g joins in the there-necked flask and mixes with 3.1g phosphorus tribromide (mol ratio 1: 1.5), then with an amount of anhydrous tetrahydro furan dissolving, stirred 30 minutes under the room temperature, wash twice, adopt silicagel column separate the whitening compound, productive rate is 84%, and is standby;
Synthesizing of (3) 3,5-two (4 '-benzoyl benzyloxy)-1-(4 ' (4 '-nitrostyrolene base) phenoxy group methylene radical) benzene
With the 4.0g 3 that second step made, 5-two ((4 '-benzoyl) benzyloxy) benzyl bromine is with 2.4g 4-(4 '-hydroxystyrene based) oil of mirbane, 0.9gK
2CO
3Join in there-necked flask at 1: 1.5: 1 with mol ratio and to mix, an amount of then anhydrous propanone dissolving was stirred 12 hours under the room temperature, filtered out precipitation, the filtrate decompression distillation, adopt silicagel column separate yellow compound, productive rate is 53%.
Embodiment 3
With 1 * 10
-53 of mol/L, 5-two (4 ' (4 '-nitrostyrolene base) benzyloxy)-1-(4 '-benzoyl benzyloxy methylene radical) benzene is dissolved in the methylene dichloride, measures its ultraviolet-visible absorption spectroscopy, absorbs to may extend to the 430nm place, as Fig. 1.
Embodiment 4
With 1 * 10
-53 of mol/L, 5-two (4 '-benzoyl benzyloxy)-1-(4 ' (4 '-nitrostyrolene base) phenoxy group methylene radical) benzene is dissolved in the methylene dichloride, measures its ultraviolet-visible absorption spectroscopy, absorbs to may extend to the 460nm place, as Fig. 2.
Embodiment 5
3, methyl methacrylate polymerization in the visible light photo sensitized initiation solution of 5-two (4 ' (4 '-nitrostyrolene base) benzyloxy)-1-(4 '-benzoyl benzyloxy methylene radical) benzene
In the long horminess glass tube of 10cm, add the ethyl acetate of 2g and the methyl methacrylate of 5 grams, the initiator that adds the invention of 10mg, the 2mL trolamine led to argon gas 20 minutes in the lucifuge situation, under the room temperature as for illumination under the tungsten-iodine lamp of 1kw, after 1 hour,, can obtain white polymer with cold methanol extraction, polymethylmethacrylate, productive rate 62%.
Embodiment 6
3,5-two (4 '-benzoyl benzyloxy)-1-(4 ' (4 '-nitrostyrolene base) phenoxy group methylene radical) benzene) methyl methacrylate polymerization in the visible light photo sensitized initiation solution
In the long horminess glass tube of 10cm, add the ethyl acetate of 2g and the methyl methacrylate of 5g, the initiator that adds the invention of 10mg, the 2mL trolamine led to argon gas 20 minutes in the lucifuge situation, under the room temperature as for illumination under the tungsten-iodine lamp of 1kw, after 1 hour,, can obtain white polymer with cold methanol extraction, polymethylmethacrylate, productive rate 68%.
Claims (3)
1. contain benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene, its typical chemical structure of general formula is:
N in the molecular structural formula (I), (II) wherein
1And n
2All represent 1-6.
2. claim 1 is described contains benzophenone fragment and to the synthetic method of the segmental dendritic visible light light trigger of nitro toluylene (I), its feature may further comprise the steps:
The first step: 3,5-two ((4 '-nitrostyrolene base) benzene-oxyl) phenylcarbinol synthetic:
Compound with structural formula (III) representative, with 3,5-dihydroxybenzyl alcohol, basic catalyst join in there-necked flask with mol ratio and mix at 3: 1: 2, then with an amount of anhydrous propanone dissolving, stir about is 12 hours under the room temperature, filters out precipitation, the filtrate decompression distillation, adopt silicagel column separate yellow compound, standby;
Second step: contain benzophenone fragment and synthesizing to the segmental dendritic visible light light trigger of nitro toluylene (I):
With the first step make 3,5-two ((4 '-nitrostyrolene base) benzene-oxyl) phenylcarbinol joins in there-necked flask with mol ratio with 4-brooethyl benzophenone and basic catalyst and mixes at 1: 1.5: 1, then with an amount of anhydrous propanone dissolving, stir about is 12 hours under the room temperature, filter out precipitation, filtrate decompression distillation, adopt silicagel column separate yellow compound;
Claim 1 is described to contain benzophenone fragment and to the synthetic method of the segmental dendritic visible light light trigger of nitro toluylene (II), its feature may further comprise the steps:
The first step: 3,5-two ((4 '-benzoyl) benzene-oxyl) phenylcarbinol synthetic:
Compound with structural formula (IV) representative, with 3,5-dihydroxybenzyl alcohol, basic catalyst join in there-necked flask with mol ratio and mix at 3: 1: 2, then with an amount of anhydrous propanone dissolving, stir about is 12 hours under the room temperature, filters out precipitation, the filtrate decompression distillation, adopt silicagel column separate yellow compound, standby;
Second step: 3,5-two ((4 '-benzoyl) benzene-oxyl) benzyl bromine synthetic:
With the first step make 3,5-two ((4 '-benzoyl) benzene-oxyl) phenylcarbinol and phosphorus tribromide join in the there-necked flask with 1: 1.5 mol ratio and mix, then with an amount of anhydrous tetrahydro furan dissolving, stir about is 30 minutes under the room temperature, wash twice, adopt silicagel column separate the whitening compound, standby;
The 3rd step: contain benzophenone fragment and synthesizing to the segmental dendritic visible light light trigger of nitro toluylene (II):
With second the step make 3; 5-two ((4 '-benzoyl) benzene-oxyl) benzyl bromine joins in there-necked flask with mol ratio with 4-(4 '-hydroxystyrene based) oil of mirbane, basic catalyst and mixes at 1: 1.5: 1; then with an amount of anhydrous propanone dissolving; stir about is 12 hours under the room temperature; filter out precipitation; filtrate decompression distillation, adopt silicagel column separate yellow compound.
3. claim 1 is described contains benzophenone fragment and to the segmental dendritic visible light light trigger of nitro toluylene, its purposes is: be used for the visible light polymerization of solution vinyl monomer as light trigger.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980392A (en) * | 2014-05-16 | 2014-08-13 | 重庆大学 | Star-like visible light initiator having conjugated structure and containing benzophenone fragments as well as synthesis and application of visible light initiator |
| CN106478843A (en) * | 2016-09-21 | 2017-03-08 | 同济大学 | A kind of double oxime ester lightlike initiating agents containing thiphene ring and its preparation method and application |
| CN109776757A (en) * | 2019-01-15 | 2019-05-21 | 陕西科技大学 | A kind of preparation method and applications of the paper surface polyurethane fluorescent brightening lotion containing benzophenone |
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| US20070287105A1 (en) * | 2006-06-09 | 2007-12-13 | Canon Kabushiki Kaisha | Photosensitive compound, photosensitive composition, method for resist pattern formation, and process for device production |
| CN100422194C (en) * | 2006-06-19 | 2008-10-01 | 浙江大学 | Siloxane precursor linked with branch-shaped azo chromophore and its synthesis method |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980392A (en) * | 2014-05-16 | 2014-08-13 | 重庆大学 | Star-like visible light initiator having conjugated structure and containing benzophenone fragments as well as synthesis and application of visible light initiator |
| CN106478843A (en) * | 2016-09-21 | 2017-03-08 | 同济大学 | A kind of double oxime ester lightlike initiating agents containing thiphene ring and its preparation method and application |
| CN106478843B (en) * | 2016-09-21 | 2017-12-26 | 同济大学 | A kind of double oxime ester lightlike initiating agents containing thiphene ring and its preparation method and application |
| CN109776757A (en) * | 2019-01-15 | 2019-05-21 | 陕西科技大学 | A kind of preparation method and applications of the paper surface polyurethane fluorescent brightening lotion containing benzophenone |
| CN109776757B (en) * | 2019-01-15 | 2021-06-08 | 陕西科技大学 | Preparation method and application of benzophenone-containing paper surface polyurethane fluorescent whitening emulsion |
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Application publication date: 20110112 |