CN103396502B - A kind of light trigger and preparation method thereof - Google Patents
A kind of light trigger and preparation method thereof Download PDFInfo
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- CN103396502B CN103396502B CN201310312267.XA CN201310312267A CN103396502B CN 103396502 B CN103396502 B CN 103396502B CN 201310312267 A CN201310312267 A CN 201310312267A CN 103396502 B CN103396502 B CN 103396502B
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Abstract
The present invention relates to a kind of light trigger and preparation method thereof.A kind of light trigger, its chemical structural formula is as follows:
Description
Technical field
The present invention relates to a kind of light trigger and preparation method thereof.
Background technology
The widespread use of light trigger Tu Liao ﹑ ink industry.Along with the raising of people's living standard, environment and food-safety problem are more and more paid attention to.The multicolor printing of packing business, especially food packaging industry, to noxious volatile organism (VOC), as benzene, tetracol phenixin, chloroform etc. have clear and definite limitation.The maximum limit of benzene burst size is 3mg/m with regard to strict regulation for the printing of such as food product pack
2, be 0.01mg/m in tobacco package
2.Past, for the light trigger of field of food, as benzophenone etc., owing to there being volatile benzene to discharge in use procedure, making it use and is limited greatly.Therefore the focus that the low new light trigger of benzene burst size becomes people's concern is developed.
Summary of the invention
Based on this, be necessary the light trigger providing a kind of benzene burst size low.
Further, the preparation method of light trigger that a kind of benzene burst size is low is provided.
A kind of light trigger, its chemical structural formula is as follows:
A kind of photocuring system, contains:
Polyalcohol acrylate;
Epoxy acrylate;
Organic amine;
Above-mentioned light trigger.
Wherein in an embodiment, described photocuring system, by percentage to the quality, containing following component:
Wherein in an embodiment, described photocuring system, by percentage to the quality, containing following component:
Wherein in an embodiment, described organic amine is P115 reactive amines.
Wherein in an embodiment, described polyalcohol acrylate is Viscoat 295.
A preparation method for light trigger, comprises the steps:
Be 4-p t butylbenzoic acid and the sulfur oxychloride mixing of 0.10:0.10 ~ 0.20 by mol ratio, stir 1 ~ 8 hour at 10 ~ 50 DEG C, remove excessive sulfur oxychloride, obtain 4-tert-butyl benzoyl chloride;
Described 4-tert-butyl benzoyl chloride is added in organic solvent, continue to be stirred to and mix, add biphenyl and obtain mixed solution, described mixed solution is cooled to-20 ~ 15 DEG C, adds aluminum chloride, be warming up to stirring at room temperature 1 ~ 3 hour, continue to be warming up to 40 DEG C to stir 0.5 ~ 1 hour, obtain reaction solution, wherein, the mol ratio of described biphenyl and described 4-tert-butyl benzoyl chloride is 0.92 ~ 0.96:1; And
Obtain above-mentioned light trigger by after reaction solution separation and purification, its chemical structural formula is as follows:
Wherein in an embodiment, described organic solvent is methylene dichloride, 1,2-ethylene dichloride, dioxane, butyl ether or 4-chlorobutane.
Wherein in an embodiment, the mol ratio of described aluminum chloride and described biphenyl is 3:1.
Wherein in an embodiment, to obtain in the step of above-mentioned light trigger after reaction solution separation and purification, the method of separation and purification is specially: pour in frozen water by reaction solution while stirring, stratification, get organic layer, described organic layer mixture of ice and water washing, in neutral, remove organic solvent, obtains the above-mentioned light trigger of purifying after drying.
Above-mentioned light trigger, owing to not having independently phenyl group in molecule, effectively reduces the burst size of benzene.
Accompanying drawing explanation
Fig. 1 is preparation method's schema of the light trigger of an embodiment.
Embodiment
For enabling above-mentioned purpose of the present invention, feature and advantage become apparent more, are described in detail the specific embodiment of the present invention below in conjunction with accompanying drawing.Set forth a lot of detail in the following description so that fully understand the present invention.But the present invention can be much different from alternate manner described here to implement, those skilled in the art can when without prejudice to doing similar improvement when intension of the present invention, therefore the present invention is by the restriction of following public concrete enforcement.
A kind of light trigger, its chemical structural formula is as follows:
Above-mentioned light trigger, owing to not having independently phenyl group in molecule, effectively reduces the burst size of benzene.
A kind of photocuring system, contains:
Polyalcohol acrylate;
Epoxy acrylate;
Organic amine; And
Light trigger.
Wherein, described polyalcohol acrylate is Viscoat 295.By percentage to the quality, the content of polyalcohol acrylate is 29 ~ 56%, and preferably, the content of polyalcohol acrylate is 45%.
Wherein, by percentage to the quality, the content of described epoxy acrylate is 35 ~ 55%, and preferably, the content of epoxy acrylate is 40%.
Wherein, described organic amine is P115 reactive amines.By percentage to the quality, the content of organic amine is 6 ~ 10%, and preferably, the content of organic amine is 10%.
Wherein, described P115 reactive amines is the aliphatic tertiary amine of Viscoat 295 esterification.
Wherein, described light trigger is the following light trigger of chemical structural formula, or the mixed light initiator containing the following light trigger of chemical structural formula and other light triggers.By percentage to the quality, the content of light trigger is 3 ~ 6%, and preferably, the content of light trigger is 5%.
Above-mentioned photocuring system, surface cure is fast, and low smell, yellowing resistance is good.
Refer to Fig. 1, the preparation method of the light trigger of an embodiment, comprises the steps:
S110, be 4-p t butylbenzoic acid and the sulfur oxychloride mixing of 0.10:0.10 ~ 0.20 by mol ratio, stir 1 ~ 8 hour at 10 ~ 50 DEG C, remove excessive sulfur oxychloride, obtain 4-tert-butyl benzoyl chloride.
Preferably, the method removing excessive sulfur oxychloride is: rotate in 50 ~ 100 DEG C of decompressions and boil off excessive sulfur oxychloride.
S120,4-tert-butyl benzoyl chloride is added in organic solvent, continue to be stirred to and mix, add biphenyl and obtain mixed solution, described mixed solution is cooled to-20 ~ 15 DEG C, adds aluminum chloride, be warming up to stirring at room temperature 1 ~ 3 hour, continue to be warming up to 40 DEG C to stir 0.5 ~ 1 hour, obtain reaction solution, wherein, the mol ratio of biphenyl and 4-tert-butyl benzoyl chloride is 0.92 ~ 0.96:1.
Preferably, add the mode of aluminum chloride for add several times, specifically in this enforcement side, divide and add for four times.
Preferably, organic solvent is methylene dichloride, 1,2-ethylene dichloride, dioxane, butyl ether or 4-chlorobutane.
The mol ratio of described aluminum chloride and described biphenyl is 3:1.
S130, obtain light trigger by after described reaction solution separation and purification, its chemical structural formula is as follows:
The method of separation and purification is specially: slowly poured in frozen water by described reaction solution while stirring, stratification, is separated removing water layer, gets the washing of organic layer frozen water in neutral, steams except organic solvent, obtain the above-mentioned light trigger of purifying after drying.
Be appreciated that the method for separation and purification is not limited to aforesaid method, the method for separation and purification can be carried out to above-mentioned reaction product all passable.
The preparation method of above-mentioned light trigger is simple, aftertreatment simple, meets environmental protection requirement.
It is below specific embodiment.
Embodiment 1
The synthesis of light trigger, its chemical structural formula is as follows:
Be that 4-p t butylbenzoic acid and the sulfur oxychloride of 0.10:0.20 joins in reaction vessel by mol ratio, stir 8 hours at 50 DEG C, rotate in 50 DEG C of decompressions and boil off excessive sulfur oxychloride, obtain 4-tert-butyl benzoyl chloride.In above-mentioned reaction vessel, add the methylene dichloride of 100 milliliters, continue to be stirred to and mix, add biphenyl and obtain mixed solution, the mol ratio of biphenyl and 4-tert-butyl benzoyl chloride is 0.92:1.Mixed solution is cooled to 15 DEG C, divide and add aluminum chloride four times, the mol ratio of aluminum chloride and described biphenyl is 3:1.Be warming up to stirring at room temperature 3 hours, continue to be warming up to 40 DEG C and stir 1 hour, obtain reaction solution.While stirring reaction solution is slowly poured in the mixture of 250 grams of ice and 50 milliliters of frozen water, stratification, be separated removing water layer, get organic layer 80 milliliters of frozen water washings repeatedly, until in neutral, steam except organic solvent, after drying, obtain the above-mentioned light trigger of purifying.
Structural Identification:
1hNMR(300 megahertz, CDCl
3), 1.43 (s, 9H), 7.46 (d; J=6.3Hz, 1H), 7.50 (d; J=9.3Hz, 2H), 7.55 (d, J=9.6Hz; 2H), 7.68-7.76 (s, 4H); 7.87 (d, J=8.4Hz, 2H); 7.96 (d, J=8.1Hz, 2H);
13cNMR(75 megahertz, CDCl
3), 31.2,35.2,125.3,126.9,127.3,128.2,128.9,129.0,130.1,130.7,131.4,135.0,136.6,140.1,145.0,156.2,196.0.ESI-Ms, m/z315.2 [M+H]
+.
Photocuring system containing above-mentioned light trigger, with XX percentages, containing following component:
By the photocuring reagent of joining by said components, with printability instrument coating about 15 micron thickness on paper blank, with the ultra violet lamp coating of 50W/CM power.
Adopt Headspace-Gas Chromatography Analysis to measure the burst size of benzene in VOC project after coating curing, measurement result is as follows:
The synthesis of embodiment 2 light trigger, its chemical structural formula is as follows:
Be that 4-p t butylbenzoic acid and the sulfur oxychloride of 0.10:0.10 joins in reaction vessel by mol ratio, stir 1 hour at 10 DEG C, rotate in 100 DEG C of decompressions and boil off excessive sulfur oxychloride, obtain 4-tert-butyl benzoyl chloride.In above-mentioned reaction vessel, add the dioxane of 30 milliliters, continue to be stirred to and mix, add biphenyl and obtain mixed solution, the mol ratio of biphenyl and 4-tert-butyl benzoyl chloride is 0.96:1.Mixed solution is cooled to-20 DEG C, and divide and add aluminum chloride three times, the mol ratio of aluminum chloride and described biphenyl is 3:1.Be warming up to stirring at room temperature 1 hour, continue to be warming up to 40 DEG C and stir 0.5 hour, obtain reaction solution.While stirring reaction solution is slowly poured in the mixture of 250 grams of ice and 50 milliliters of frozen water, stratification, be separated removing water layer, get organic layer 80 milliliters of frozen water washings repeatedly, until in neutral, steam except organic solvent, after drying, obtain the above-mentioned light trigger of purifying.
Structural Identification:
1hNMR(300 megahertz, CDCl
3), 1.43 (s, 9H), 7.46 (d; J=6.3Hz, 1H), 7.50 (d; J=9.3Hz, 2H), 7.55 (d, J=9.6Hz; 2H), 7.68-7.76 (s, 4H); 7.87 (d, J=8.4Hz, 2H); 7.96 (d, J=8.1Hz, 2H);
13cNMR(75 megahertz, CDCl
3), 31.2,35.2,125.3,126.9,127.3,128.2,128.9,129.0,130.1,130.7,131.4,135.0,136.6,140.1,145.0,156.2,196.0.ESI-Ms, m/z315.2 [M+H]
+.
Photocuring system containing above-mentioned light trigger, by percentage to the quality, containing following component:
By the photocuring reagent of joining by said components, get over 15 micron thickness on paper blank, with the ultra violet lamp coating of 50W/CM power with the coating of printability instrument.
Adopt Headspace-Gas Chromatography Analysis to measure the burst size of benzene in VOC project after coating curing, measurement result is as follows:
The synthesis of embodiment 3 light trigger, its chemical structural formula is as follows:
Be that 4-p t butylbenzoic acid and the sulfur oxychloride of 0.10:0.20 joins in reaction vessel by mol ratio, stir 4 hours at 40 DEG C, rotate in 90 DEG C of decompressions and boil off excessive sulfur oxychloride, obtain 4-tert-butyl benzoyl chloride.In above-mentioned reaction vessel, add the methylene dichloride of 50 milliliters, continue to be stirred to and mix, add biphenyl and obtain mixed solution, the mol ratio of biphenyl and 4-tert-butyl benzoyl chloride is 0.95:1.Mixed solution is cooled to 10 DEG C, divide and add aluminum chloride four times, the mol ratio of aluminum chloride and described biphenyl is 3:1.Be warming up to stirring at room temperature 3 hours, continue to be warming up to 40 DEG C and stir 1 hour, obtain reaction solution.While stirring reaction solution is slowly poured in the mixture of 250 grams of ice and 50 milliliters of frozen water, stratification, be separated removing water layer, get organic layer 80 milliliters of frozen water washings repeatedly, until in neutral, steam except organic solvent, after drying, obtain the above-mentioned light trigger of purifying.
Structural Identification:
1hNMR(300 megahertz, CDCl
3), 1.43 (s, 9H), 7.46 (d; J=6.3Hz, 1H), 7.50 (d; J=9.3Hz, 2H), 7.55 (d, J=9.6Hz; 2H), 7.68-7.76 (s, 4H); 7.87 (d, J=8.4Hz, 2H); 7.96 (d, J=8.1Hz, 2H);
13cNMR(75 megahertz, CDCl
3), 31.2,35.2,125.3,126.9,127.3,128.2,128.9,129.0,130.1,130.7,131.4,135.0,136.6,140.1,145.0,156.2,196.0.ESI-Ms, m/z315.2 [M+H]
+.
Photocuring system containing above-mentioned light trigger, with XX percentages, containing following component:
By the photocuring reagent of joining by said components, with printability instrument coating about 15 micron thickness on paper blank, with the ultra violet lamp coating of 50W/CM power.
Adopt Headspace-Gas Chromatography Analysis to measure the burst size of benzene in VOC project after coating curing, measurement result is as follows:
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (10)
1. a light trigger, its chemical structural formula is as follows:
2. a photocuring system, is characterized in that, contains:
Polyalcohol acrylate;
Epoxy acrylate;
Organic amine;
Light trigger as claimed in claim 1.
3. photocuring system as claimed in claim 2, is characterized in that, by percentage to the quality, containing following component:
4. photocuring system as claimed in claim 2, is characterized in that, by percentage to the quality, containing following component:
5. photocuring system as claimed in claim 2, it is characterized in that, described organic amine is P115 reactive amines.
6. photocuring system as claimed in claim 2, it is characterized in that, described polyalcohol acrylate is Viscoat 295.
7. a preparation method for light trigger, is characterized in that, comprises the steps:
Be 4-p t butylbenzoic acid and the sulfur oxychloride mixing of 0.10:0.10 ~ 0.20 by mol ratio, stir 1 ~ 8 hour at 10 ~ 50 DEG C, remove excessive sulfur oxychloride, obtain 4-tert-butyl benzoyl chloride;
Described 4-tert-butyl benzoyl chloride is added in organic solvent, continue to be stirred to and mix, add biphenyl and obtain mixed solution, described mixed solution is cooled to-20 ~ 15 DEG C, adds aluminum chloride, be warming up to stirring at room temperature 1 ~ 3 hour, continue to be warming up to 40 DEG C to stir 0.5 ~ 1 hour, obtain reaction solution, wherein, the mol ratio of described biphenyl and described 4-tert-butyl benzoyl chloride is 0.92 ~ 0.96:1; And
Obtain light trigger as claimed in claim 1 by after reaction solution separation and purification, its chemical structural formula is as follows:
8. the preparation method of light trigger as claimed in claim 7, it is characterized in that, described organic solvent is methylene dichloride, 1,2-ethylene dichloride, dioxane, butyl ether or 4-chlorobutane.
9. the preparation method of light trigger as claimed in claim 7, it is characterized in that, the mol ratio of described aluminum chloride and described biphenyl is 3:1.
10. the preparation method of light trigger as claimed in claim 7, it is characterized in that, to obtain in the step of light trigger as claimed in claim 1 after reaction solution separation and purification, the method of separation and purification is specially: pour in frozen water by reaction solution while stirring, stratification, gets organic layer, and described organic layer mixture of ice and water washing is to being neutrality, removing organic solvent, obtains the light trigger as claimed in claim 1 of purifying after drying.
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| CN102766045B (en) * | 2012-07-31 | 2014-03-05 | 惠州市华泓新材料有限公司 | Benzophenone derivative and application thereof as photoinitiator |
| CN103012317B (en) * | 2012-12-23 | 2014-10-15 | 惠州市华泓新材料有限公司 | Alkyl phenyl derivative and application of alkyl phenyl derivative as photoinitiator |
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